Origin of the Red-Shifted Optical Spectra Recorded for Aza-BODIPY Dyes

Karlsson, Joshua K. G.; Harriman, Anthony

doi:10.1021/acs.jpca.6b01278

Cited by 68Luminescence and Fluorescent MaterialsPorphyrin and Phthalocyanine ChemistryPhotochemistry and Electron Transfer Studies

Origin of the Red-Shifted Optical Spectra Recorded for Aza-BODIPY Dyes

Open access

Karlsson, Joshua K. G., Harriman, Anthony·2016·The Journal of Physical Chemistry A

DOI 10.1021/acs.jpca.6b01278

Open this paper in CoChat — free account

Abstract

The optical properties are compared for two boron dipyrromethene (BODIPY) dyes that differ by virtue of the substituent at the meso-site, namely, aza-N versus C-methine atoms. Both compounds are equipped with aryl rings at the 3- and 5-positions of the dipyrrin backbone, which help to extend the degree of π-delocalization. The aza-BODIPY dye absorbs and fluoresces at much lower energy than does the conventional BODIPY dye, with red shifts of about 100 nm being observed in fluid solution, but with comparable fluorescence yield and lifetime. Hydrogen bonding donors, such as alcohols, attach to the aza-N atom and promote nonradiative decay without affecting the properties of the conventional dye. Triplet formation is ineffective in the absence of a spin-orbit coupler. Quantum chemical calculations indicate that the electronegative aza-N atom lowers the energy of the LUMO while having little effect on the corresponding HOMO energy. The resultant decrease in the HOMO-LUMO energy gap is primarily responsible for the red shift. The HOMO-LUMO energy gap is also affected by the dihedral angle subtended by the aryl rings, but this is insensitive to the geometry around the central 6-membered ring. The aza-N atom, by virtue of restricting spatial overlap between the HOMO and LUMO, decreases the energy gap between excited-singlet and -triplet states.

Integrity signals

Registry

Crossref · 10.1021/acs.jpca.6b01278

Cites

72 of 72 references verified0 citation errors · 0 not checkable

Statistics

Recomputing p-values needs the paper’s full text.

Claims the paper makes

We couldn’t retrieve this paper’s full text, so its claims and self-check weren’t run. The registry and citation checks still apply.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

Replacing the meso-methine group in the acceptor BODIPY core with an aza-N atom gives an additional red shift in both absorption and fluorescence transitions.
“By replacing the meso-methine group in the acceptor BODIPY core with an aza-N atom, an additional red shift in both absorption and fluorescence transitions was achieved.62”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [62]

Principles of Fluorescence Spectroscopy
Lakowicz, J. R. (2006) · Springer eBooks · doi:10.1007/978-0-387-46312-4 · Cited by 19,375 · see citing works
A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP)
Yanai, T., Tew, D. P., & Handy, N. C. (2004) · Chemical Physics Letters · doi:10.1016/j.cplett.2004.06.011 · Cited by 15,047 · see citing works
New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening
Skehan, P., Storeng, R., Scudiero, D. A., Monks, A. P., McMahon, J., Vistica, D. T., Warren, J. T., Bokesch, H. R., Kenney, S., & Boyd, M. R. (1990) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/82.13.1107 · Cited by 9,801 · see citing works
Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon
Woon, D. E., & Dunning, T. H. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464303 · Cited by 9,612 · see citing works
BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties
Loudet, A., & Burgess, K. (2007) · Chemical Reviews · doi:10.1021/cr078381n · Cited by 5,238 · see citing works
Molecular Fluorescence
Valeur, B., & Berberan-Santos, M. N. (2012) · Wiley eBooks · doi:10.1002/9783527650002 · Cited by 4,109 · see citing works
Optimization of parameters for semiempirical methods V: Modification of NDDO approximations and application to 70 elements
Stewart, J. J. P. (2007) · Journal of Molecular Modeling · doi:10.1007/s00894-007-0233-4 · Cited by 3,652 · see citing works
The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed
Ulrich, G., Ziessel, R. F., & Harriman, A. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200702070 · Cited by 3,171 · see citing works
Self-citation
The Fluorescent Toolbox for Assessing Protein Location and Function
Giepmans, B. N. G., Adams, S., Ellisman, M. H., & Tsien, R. Y. (2006) · Science · doi:10.1126/science.1124618 · Cited by 2,782 · see citing works
The energy gap law for radiationless transitions in large molecules
Englman, R., & Jortner, J. (1970) · Molecular Physics · doi:10.1080/00268977000100171 · Cited by 2,778 · see citing works
J‐Aggregates: From Serendipitous Discovery to Supramolecular Engineering of Functional Dye Materials
Würthner, F., Kaiser, T. E., & Saha‐Möller, C. R. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201002307 · Cited by 2,597 · see citing works
Relationship between Absorption Intensity and Fluorescence Lifetime of Molecules
Strickler, S. J., & Berg, R. A. (1962) · The Journal of Chemical Physics · doi:10.1063/1.1733166 · Cited by 2,504 · see citing works
New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution
Cossi, M., Scalmani, G., Rega, N., & Barone, V. (2002) · The Journal of Chemical Physics · doi:10.1063/1.1480445 · Cited by 2,397 · see citing works
Toward a systematic molecular orbital theory for excited states
Foresman, J. B., Head‐Gordon, M., Pople, J. A., & Frisch, M. J. (1992) · The Journal of Physical Chemistry · doi:10.1021/j100180a030 · Cited by 2,388 · see citing works
Fluorescent indicators based on BODIPY
Boens, N., Leen, V., & Dehaen, W. (2011) · Chemical Society Reviews · doi:10.1039/c1cs15132k · Cited by 2,271 · see citing works
BODIPY dyes in photodynamic therapy
Kamkaew, A., Lim, S. H., Lee, H. B., Kiew, L. V., Chung, L. Y., & Burgess, K. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35216h · Cited by 2,104 · see citing works
Super-resolution fluorescence microscopy
Huang, B., Bates, M., & Zhuang, X. (2009) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.77.061906.092014 · Cited by 1,657 · see citing works
Hydrogen Bonding in the Electronic Excited State
Zhao, G.-J., & Han, K. (2011) · Accounts of Chemical Research · doi:10.1021/ar200135h · Cited by 1,394 · see citing works
Fluoro-Jade B: a high affinity fluorescent marker for the localization of neuronal degeneration
Schmued, L. C., & Hopkins, K. J. (2000) · Brain Research · doi:10.1016/s0006-8993(00)02513-0 · Cited by 1,218 · see citing works
Molecular Rotor Measures Viscosity of Live Cells via Fluorescence Lifetime Imaging
Kuimova, M. K., Yahioglu, G., Levitt, J. A., & Suhling, K. (2008) · Journal of the American Chemical Society · doi:10.1021/ja800570d · Cited by 822 · see citing works
Characterization of PicoGreen Reagent and Development of a Fluorescence-Based Solution Assay for Double-Stranded DNA Quantitation
Singer, V. L., Jones, L. J., Yue, S. T., & Haugland, R. P. (1997) · Analytical Biochemistry · doi:10.1006/abio.1997.2177 · Cited by 780 · see citing works
NIR dyes for bioimaging applications
Escobedo, J. O., Rusin, O., Lim, S., & Strongin, R. M. (2009) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2009.10.022 · Cited by 765 · see citing works
A doubles correction to electronic excited states from configuration interaction in the space of single substitutions
Head‐Gordon, M., Rico, R. J., Oumi, M., & Lee, T. J. (1994) · Chemical Physics Letters · doi:10.1016/0009-2614(94)00070-0 · Cited by 699 · see citing works
Cyanine dyes in biophysical research: the photophysics of polymethine fluorescent dyes in biomolecular environments
Levitus, M., & Ranjit, S. (2010) · Quarterly Reviews of Biophysics · doi:10.1017/s0033583510000247 · Cited by 437 · see citing works
A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue
Yoon, S., Miller, E. W., He, Q., Patrick, H., & Chang, C. J. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200701785 · Cited by 390 · see citing works
3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes: Synthesis, Spectroscopic, Electrochemical, and Structural Properties
Burghart, A., Kim, H., Welch, M. B., Thoresen, L. H., Reibenspies, J., Burgess, K., Bergström, F., & Johansson, L. B. ‐. (1999) · The Journal of Organic Chemistry · doi:10.1021/jo990796o · Cited by 369 · see citing works
Photochemical heavy-atom effects
Koziar, J. C., & Cowan, D. O. (1978) · Accounts of Chemical Research · doi:10.1021/ar50129a003 · Cited by 344 · see citing works
A DFT/TDDFT interpretation of the ground and excited states of porphyrin and porphyrazine complexes
Baerends, E. J., Ricciardi, G., Rosa, A., & van Gisbergen, S. J. A. (2002) · Coordination Chemistry Reviews · doi:10.1016/s0010-8545(02)00093-0 · Cited by 314 · see citing works
Conformationally Restricted Aza‐Bodipy: A Highly Fluorescent, Stable, Near‐Infrared‐Absorbing Dye
Zhao, W., & Carreira, E. M. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200461868 · Cited by 301 · see citing works
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations
Chen, J., Burghart, A., Derecskei‐Kovacs, A., & Burgess, K. (2000) · The Journal of Organic Chemistry · doi:10.1021/jo991927o · Cited by 278 · see citing works
Calculation of UV/Vis Spectra in Solution
Klamt, A. (1996) · The Journal of Physical Chemistry · doi:10.1021/jp950607f · Cited by 262 · see citing works
Site-Selective Fluorescence Spectroscopy of Conjugated Polymers and Oligomers
Bässler, H., & Schweitzer, B. (1998) · Accounts of Chemical Research · doi:10.1021/ar960228k · Cited by 262 · see citing works
Conformationally Restricted Aza‐Bodipy: A Highly Fluorescent, Stable, Near‐Infrared‐Absorbing Dye
Zhao, W., & Carreira, E. M. (2005) · Angewandte Chemie · doi:10.1002/ange.200461868 · Cited by 251 · see citing works
Photophysical properties of porphyrins in biological membranes
Ricchelli, F. (1995) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/1011-1344(95)07155-u · Cited by 249 · see citing works
Boron Dipyrromethene Chromophores: Next Generation Triplet Acceptors/Annihilators for Low Power Upconversion Schemes
Singh-Rachford, T. N., Haefelé, A., Ziessel, R. F., & Castellano, F. N. (2008) · Journal of the American Chemical Society · doi:10.1021/ja807056a · Cited by 241 · see citing works
Influence Of Electronic Delocalization In Metal-to-Ligand Charge Transfer Excited States
Strouse, G. F., Schoonover, J. R., Duesing, R., Boyde, S., Jones, W. E. J., & Meyer, T. J. (1995) · Inorganic Chemistry · doi:10.1021/ic00106a009 · Cited by 227 · see citing works
Understanding the Control of Singlet-Triplet Splitting for Organic Exciton Manipulating: A Combined Theoretical and Experimental Approach
Chen, T., Zheng, L., Yuan, J., An, Z., Chen, R., Tao, Y., Li, H., Xie, X., & Huang, W. (2015) · Scientific Reports · doi:10.1038/srep10923 · Cited by 219 · see citing works
Why Do TD-DFT Excitation Energies of BODIPY/Aza-BODIPY Families Largely Deviate from Experiment? Answers from Electron Correlated and Multireference Methods
Momeni, M. R., & Brown, A. (2015) · Journal of Chemical Theory and Computation · doi:10.1021/ct500775r · Cited by 219 · see citing works
Fluorescent labels for proteomics and genomics
Waggoner, A. S. (2006) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2006.01.005 · Cited by 214 · see citing works
An Artificial Light-Harvesting Array Constructed from Multiple Bodipy Dyes
Ziessel, R. F., Ulrich, G., Haefelé, A., & Harriman, A. (2013) · Journal of the American Chemical Society · doi:10.1021/ja4049306 · Cited by 204 · see citing works
Self-citation
Synthesis and spectroscopic properties of a new 4-bora-3a,4a-diaza-s-indacene (BODIPY®) dye
Kim, H., Burghart, A., Welch, M. B., Reibenspies, J., & Burgess, K. (1999) · Chemical Communications · doi:10.1039/a905739k · Cited by 182 · see citing works
B , O -Chelated Azadipyrromethenes as Near-IR Probes
Loudet, A., Bandichhor, R., Burgess, K., Palma, A., McDonnell, S. O., Hall, M. J., & O’Shea, D. F. (2008) · Organic Letters · doi:10.1021/ol8018506 · Cited by 177 · see citing works
Synthesis and Characterization of Near‐Infrared Absorbing Benzannulated Aza‐BODIPY Dyes
Gresser, R., Hummert, M., Hartmann, H., Leo, K., & Riede, M. (2011) · Chemistry - A European Journal · doi:10.1002/chem.201002941 · Cited by 168 · see citing works
Replacing Phenyl Ring with Thiophene: An Approach to Longer Wavelength Aza-dipyrromethene Boron Difluoride (Aza-BODIPY) Dyes
Zhang, X., Yu, H., & Xiao, Y. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo201413b · Cited by 153 · see citing works
Improving the Accuracy of Excited-State Simulations of BODIPY and Aza-BODIPY Dyes with a Joint SOS-CIS(D) and TD-DFT Approach
Chibani, S., Laurent, A. D., Guennic, B. L., & Jacquemin, D. (2014) · Journal of Chemical Theory and Computation · doi:10.1021/ct500655k · Cited by 122 · see citing works
Rigorous Franck–Condon absorption and emission spectra of conjugated oligomers from quantum chemistry
Karabunarliev, S. H., Baumgarten, M., Bittner, E. R., & Müllen, K. (2000) · The Journal of Chemical Physics · doi:10.1063/1.1328067 · Cited by 118 · see citing works
Highly Substituted Bodipy Dyes with Spectroscopic Features Sensitive to the Environment
Bura, T., Retailleau, P., Ulrich, G., & Ziessel, R. F. (2011) · The Journal of Organic Chemistry · doi:10.1021/jo102203f · Cited by 117 · see citing works
Comparative Photostability Studies of BODIPY and Fluorescein Dyes by Using Fluorescence Correlation Spectroscopy
Hinkeldey, B., Schmitt, A., & Jung, G. (2008) · ChemPhysChem · doi:10.1002/cphc.200800299 · Cited by 112 · see citing works
Photophysical properties of porphyrins, phthalocyanines, and benzochlorins
Owens, J. W., Smith, R., Robinson, R., & Robins, M. (1998) · Inorganica Chimica Acta · doi:10.1016/s0020-1693(98)00137-6 · Cited by 101 · see citing works
Photochemistry of intercalated quaternary diazaaromatic salts
Brun, A. M., & Harriman, A. (1991) · Journal of the American Chemical Society · doi:10.1021/ja00021a047 · Cited by 87 · see citing works
Self-citation
Synthesis and Properties of BF 2 -3,3′-Dimethyldiarylazadipyrromethene Near-Infrared Fluorophores
Wu, D., & O’Shea, D. F. (2013) · Organic Letters · doi:10.1021/ol401434c · Cited by 82 · see citing works
An Oligomer Study on Small Band Gap Polymers
Karsten, B. P., Viani, L., Gierschner, J., Cornil, J., & Janssen, R. A. J. (2008) · The Journal of Physical Chemistry A · doi:10.1021/jp805817c · Cited by 73 · see citing works
BODIPY‐Tetrazine Multichromophoric Derivatives
Dumas, C., Miomandre, F., Lépicier, E., Galangau, O., Vu, T., Clavier, G. M., Méallet‐Renault, R., & Audebert, P. (2010) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200900874 · Cited by 71 · see citing works
Phosphorescence and Triplet State Energies of Oligothiophenes
Wasserberg, D., Marsal, P., Meskers, S. C. J., Janssen, R. A. J., & Beljonne, D. (2005) · The Journal of Physical Chemistry B · doi:10.1021/jp0457085 · Cited by 64 · see citing works
Effect of meso-substituents on the electronic transitions of BODIPY dyes: DFT and RI-CC2 study
Петрушенко, И. К., & Petrushenko, K. B. (2014) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2014.12.005 · Cited by 58 · see citing works
Temperature-dependent rotational relaxation of nonpolar probes in mono and diols: Size effects versus hydrogen bonding
Dutt, G. B., & Krishna, G. R. (2000) · The Journal of Chemical Physics · doi:10.1063/1.481023 · Cited by 57 · see citing works
Jahn–Teller triplet excited state structures and spectra of zinc complexes of porphyrin and phthalocyanine: A density functional theory study
Nguyen, K. A., & Pachter, R. (2003) · The Journal of Chemical Physics · doi:10.1063/1.1540627 · Cited by 50 · see citing works
Highly Systematic and Efficient HOMO–LUMO Energy Gap Control of Thiophene-Pyrazine-Acenes
Brownell, L. V., Robins, K. A., Jeong, Y., Lee, Y., & Lee, D. (2013) · The Journal of Physical Chemistry C · doi:10.1021/jp407269p · Cited by 49 · see citing works
Fluorescent molecular rotors based on the BODIPY motif: effect of remote substituents
Bahaidarah, E. A., Harriman, A., Stachelek, P., Rihn, S., Heyer, E., & Ziessel, R. F. (2014) · Photochemical & Photobiological Sciences · doi:10.1039/c4pp00204k · Cited by 47 · see citing works
Self-citation
A General Synthetic Strategy for the Design of New BODIPY Fluorophores Based on Pyrroles with Polycondensed Aromatic and Metallocene Substituents
Schmidt, E. Y., Zorina, N. V., Dvorko, M. Y., Protsuk, N. I., Belyaeva, K. V., Clavier, G. M., Méallet‐Renault, R., Vu, T., Михалева, А. Й., & Trofimov, B. A. (2011) · Chemistry - A European Journal · doi:10.1002/chem.201003242 · Cited by 38 · see citing works
External iodine atoms influence over the intersystem crossing rate of cyanine iodide ion pair in benzene solution
Sauerwein, B., & Schuster, G. B. (1991) · The Journal of Physical Chemistry · doi:10.1021/j100158a006 · Cited by 37 · see citing works
PEGylated aza-BODIPY derivatives as NIR probes for cellular imaging
Daniel, C., Vida, Y., Nájera, F., & Pérez‐Inestrosa, E. (2013) · RSC Advances · doi:10.1039/c3ra46235h · Cited by 37 · see citing works
Fluorescent boron dipyrromethene (Bodipy) dyes having two and four vinyl residues
Bura, T., Hablot, D., & Ziessel, R. (2011) · Tetrahedron Letters · doi:10.1016/j.tetlet.2011.02.094 · Cited by 31 · see citing works
Theoretical investigation of 1,1′-bi-2-naphthol isomerization
Sahnoun, R., Koseki, S., & Fujimura, Y. (2004) · Journal of Molecular Structure · doi:10.1016/j.molstruc.2004.11.041 · Cited by 31 · see citing works
An efficient method of chemical modification of BODIPY core
Zatsikha, Y. V., Yakubovskyi, V. P., Shandura, M. P., Dubey, I. Y., & Kovtun, Y. P. (2013) · Tetrahedron · doi:10.1016/j.tet.2013.01.050 · Cited by 28 · see citing works
Stepwise photoconversion of an artificial light-harvesting array built from extended BODIPY units
Harriman, A., Stachelek, P., Sutter, A., & Ziessel, R. F. (2015) · Photochemical & Photobiological Sciences · doi:10.1039/c5pp00021a · Cited by 22 · see citing works
Self-citation
Temperature dependence of photoluminescence in polyfluorene thin films—Huang–Rhys factors of as-coated, annealed and crystallized thin films
Asada, K., Kobayashi, T., & Naito, H. (2005) · Thin Solid Films · doi:10.1016/j.tsf.2005.06.077 · Cited by 21 · see citing works
Spectroscopy and laser performance of new BF 2 -complex dyes in solution
Allik, T. H., Hermes, R. E., Sathyamoorthi, G., & Boyer, J. H. (1994) · Proceedings of SPIE, the International Society for Optical Engineering/Proceedings of SPIE · doi:10.1117/12.172742 · Cited by 20 · see citing works
Comparison of electronic effects of β-aryl substituents on optical and electrochemical properties of 5,15-diazaporphyrin π-systems
Omomo, S., Furukawa, K., Nakano, H., & Matano, Y. (2015) · Journal of Porphyrins and Phthalocyanines · doi:10.1142/s1088424615500509 · Cited by 11 · see citing works
Influence of a Solvent on the Quantum Yield and Duration of the Fluorescence of Tetraazoporphin
Shushkevich, I. K., Pershukevich, P. P., Stupak, A. P., & Соловьев, К. Н. (2005) · Journal of Applied Spectroscopy · doi:10.1007/s10812-005-0146-x · Cited by 9 · see citing works
Electron–phonon interactions in poly(para-phenylene) oligomers
Lavrentiev, M. Y., & Barford, W. (1999) · The Journal of Chemical Physics · doi:10.1063/1.480474 · Cited by 6 · see citing works
Comparison of large basis set DFT and MP2 calculations in the study of the barrier for internal rotation of 2,3,5,6‐tetrafluoroanisole
Kieninger, M., Cachau, R. E., Oberhammer, H., & Ventura, O. N. (2006) · International Journal of Quantum Chemistry · doi:10.1002/qua.21071 · Cited by 4 · see citing works

Flagged first, then by citations

Sorted by citations

Bioapplications of small molecule Aza-BODIPY: from rational structural design to in vivo investigations
Shi, Z., Xu, H., Hu, W., Bai, H., Peng, B., Ji, L., Fan, Q., Li, L., & Huang, W. (2020) · Chemical Society Reviews · doi:10.1039/d0cs00234h · Cited by 474 · see citing works
Singlet fission molecules among known compounds: finding a few needles in a haystack
Padula, D., Omar, Ö. H., Nematiaram, T., & Troisi, A. (2019) · Energy & Environmental Science · doi:10.1039/c9ee01508f · Cited by 120 · see citing works
Recent advances in the synthesis of [ a ]-benzo-fused BODIPY fluorophores
Jean‐Gérard, L., Vasseur, W., Scherninski, F., & Andrioletti, B. (2018) · Chemical Communications · doi:10.1039/c8cc06403b · Cited by 115 · see citing works
Carbazole‐Linked Near‐Infrared Aza‐BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep‐Tissue Imaging
Gawale, Y., Adarsh, N., Kalva, S. K., Joseph, J., Pramanik, M., Ramaiah, D., & Sekar, N. (2017) · Chemistry - A European Journal · doi:10.1002/chem.201605702 · Cited by 100 · see citing works
Evolution of Aza-BODIPY dyes-A hot topic
Kaur, M., Janaagal, A., Balsukuri, N., & Gupta, I. (2023) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2023.215428 · Cited by 96 · see citing works
Molecular Engineering of Near-Infrared Light-Responsive BODIPY-Based Nanoparticles with Enhanced Photothermal and Photoacoustic Efficiencies for Cancer Theranostics
Gao, D., Zhang, B., Liu, Y., Hu, D., Sheng, Z., Zhang, X., & Yuan, Z. (2019) · Theranostics · doi:10.7150/thno.34418 · Cited by 72 · see citing works
A fast-response, red emission aza-BODIPY-hydrazone-based chemodosimeter for selective detection of HClO
Gao, Y., Pan, Y., He, Y., Chen, H., & Nemykin, V. N. (2018) · Sensors and Actuators B Chemical · doi:10.1016/j.snb.2018.04.135 · Cited by 41 · see citing works
An Organic Chemist's Guide to Fluorophores – Understanding Common and Newer Non‐Planar Fluorescent Molecules for Biological Applications
Lovell, T. C., Branchaud, B. P., & Jasti, R. (2024) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202301196 · Cited by 39 · see citing works
Prevalent Bioimaging Scaffolds: Synthesis, Photophysical Properties and Applications
Colas, K., Doloczki, S., Urrutia, M. P., & Dyrager, C. (2021) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202001658 · Cited by 39 · see citing works
The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates
Piwoński, H., Nozue, S., & Habuchi, S. (2022) · ACS Nanoscience Au · doi:10.1021/acsnanoscienceau.1c00038 · Cited by 39 · see citing works
Substitution at boron in BODIPYs
Gapare, R. L., & Thompson, A. (2022) · Chemical Communications · doi:10.1039/d2cc02362h · Cited by 38 · see citing works
Optical limiting properties of 3,5-diphenyldibenzo-azaBODIPY at 532 nm
Kubheka, G., Achadu, O. J., Mack, J. P., & Nyokong, T. (2017) · New Journal of Chemistry · doi:10.1039/c7nj01503h · Cited by 38 · see citing works
Photophysics and redox properties of aza-BODIPY dyes with electron-withdrawing groups
Gut, A., Łapok, Ł., Jamróz, D., Gorski, A., Solarski, J., & Nowakowska, M. (2017) · New Journal of Chemistry · doi:10.1039/c7nj02757e · Cited by 36 · see citing works
One-Pot Synthesis of a Mono-O,B,N-strapped BODIPY Derivative Displaying Bright Fluorescence in the Solid State
Sirbu, D., Benniston, A. C., & Harriman, A. (2017) · Organic Letters · doi:10.1021/acs.orglett.7b00435 · Cited by 34 · see citing works
Self-citation
Extending optical chemical tools and technologies to mice by shifting to the shortwave infrared region
Wong, K. C. Y., & Sletten, E. M. (2022) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2022.102131 · Cited by 31 · see citing works
Data‐Driven Discovery of Organic Electronic Materials Enabled by Hybrid Top‐Down/Bottom‐Up Design
Blaskovits, J. T., Laplaza, R., Vela, S., & Corminbœuf, C. (2023) · Advanced Materials · doi:10.1002/adma.202305602 · Cited by 29 · see citing works
An anthracenecarboximide fluorescent probe for in vitro and in vivo ratiometric imaging of endogenous alpha- l -fucosidase for hepatocellular carcinoma diagnosis
Hou, X., Jin, P., Zeng, F., Yu, C., & Wu, S. (2016) · Materials Chemistry Frontiers · doi:10.1039/c6qm00112b · Cited by 29 · see citing works
Elucidating the Relationship between Multiradical Character and Predicted Singlet Fission Activity
Omar, Ö. H., Padula, D., & Troisi, A. (2020) · ChemPhotoChem · doi:10.1002/cptc.202000098 · Cited by 28 · see citing works
Investigating the excited state optical properties and origin of large stokes shift in Benz[c,d]indole N-Heteroarene BF2 dyes with ab initio tools
Gawale, Y., & Sekar, N. (2017) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2017.12.006 · Cited by 28 · see citing works
Effect of the Aza-N-Bridge and Push–Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs
Schäfer, C., Mony, J., Olsson, T., & Börjesson, K. (2022) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.1c02525 · Cited by 27 · see citing works
Electronic Communication in Closely Connected BODIPY-Based Bichromophores
Stachelek, P., & Harriman, A. (2016) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.6b08284 · Cited by 26 · see citing works
Self-citation
Structure Based Modulation of Electron Dynamics in meso-(4-Pyridyl)-BODIPYs: A Computational and Synthetic Approach
LaMaster, D. J., Kaufman, N. E. M., Bruner, A., & Vicente, M. G. H. (2018) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.8b05153 · Cited by 23 · see citing works
Tetraphenylethylene- and fluorene-functionalized near-infrared aza-BODIPY dyes for living cell imaging
Zhu, L., Xie, W., Zhao, L., Zhang, Y., & Chen, Z. (2017) · RSC Advances · doi:10.1039/c7ra10820f · Cited by 23 · see citing works
Synthesis and photophysical properties of monomeric and dimeric halogenated aza-BODIPYs
Çınar, H. Ş., Özçelik, Ş., Kaya, K., Kutlu, Ö. D., Erdoğmuş, A., & Gül, A. (2019) · Journal of Molecular Structure · doi:10.1016/j.molstruc.2019.127108 · Cited by 21 · see citing works
Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands
Diaz‐Rodriguez, R. M., Robertson, K. N., & Thompson, A. (2019) · Dalton Transactions · doi:10.1039/c9dt01148j · Cited by 21 · see citing works
Reunderstanding the Fluorescent Behavior of Four-Coordinate Monoboron Complexes Containing Monoanionic Bidentate Ligands
Qi, Y., Kang, R., Huang, J., Zhang, W., He, G., Yin, S., & Fang, Y. (2017) · The Journal of Physical Chemistry B · doi:10.1021/acs.jpcb.7b02405 · Cited by 20 · see citing works
Enhancing Near‐Infrared Two‐Photon Absorption of Aza‐Boron‐Dipyrromethene Compounds Through Intramolecular Charge Transfer Via Electron Donating Substitution
Doğan, A., Yılmaz, H., Karatay, A., Yıldız, E. A., Sevinç, G., Ünver, H., Boyacıoğlu, B., Hayvalı, M., & Elmalı, A. (2025) · ChemPlusChem · doi:10.1002/cplu.202500354 · Cited by 19 · see citing works
Surface roughness effect on the cellular uptake of layered double hydroxide nanoparticles
Kim, H.-J., Kim, S. H., Kim, H., Kim, Y. S., & Oh, J. (2021) · Applied Clay Science · doi:10.1016/j.clay.2021.105992 · Cited by 18 · see citing works
Synthesis, Structure and Photophysical Properties of a New Class of Inherently Chiral Boron(III) Chelates—The tert‐Leucine Complexes
Algoazy, N., Knight, J. G., Waddell, P. G., Aerts, R., Herrebout, W., Al‐Sharif, H. H. T., Karlsson, J. K. G., & Harriman, A. (2020) · Chemistry - A European Journal · doi:10.1002/chem.202005246 · Cited by 17 · see citing works
Self-citation
Self‐Assembled (Aza)BODIPY Dyes for Biomedical in Vivo Imaging
Albers, A., Masthoff, M., & Fernández, G. (2026) · Angewandte Chemie International Edition · doi:10.1002/anie.202525491 · Cited by 16 · see citing works
A fluorescence nanoscopy marker for corticotropin-releasing hormone type 1 receptor: computer design, synthesis, signaling effects, super-resolved fluorescence imaging, and in situ affinity constant in cells
Szalai, A. M., Armando, N. G., Barabas, F. M., Stefani, F. D., Giordano, L., Bari, S. E., Cavasotto, C. N., Silberstein, S., & Aramendía, P. F. (2018) · Physical Chemistry Chemical Physics · doi:10.1039/c8cp06196c · Cited by 15 · see citing works
Cyanine dyes as ratiometric fluorescence standards for the far-red spectral region
Karlsson, J. K. G., Woodford, O. J., Mustroph, H., & Harriman, A. (2017) · Photochemical & Photobiological Sciences · doi:10.1039/c7pp00333a · Cited by 14 · see citing works
Self-citation
Quantum Chemical Study Aimed at Modeling Efficient Aza-BODIPY NIR Dyes: Molecular and Electronic Structure, Absorption, and Emission Spectra
Pogonin, A. E., Shagurin, A., Savenkova, M. A., Telegin, F. Y., Marfin, Y. S., & Вашурин, А. С. (2020) · Molecules · doi:10.3390/molecules25225361 · Cited by 14 · see citing works
Polypyridyl substituted BODIPY derivatives; water switchable imaging probes that exhibit halogen substituent dependent localisation in live cells
Dolan, C., Byrne, A., Long, C., Czamara, K., Kaczor, A., Barańśka, M., & Keyes, T. E. (2017) · RSC Advances · doi:10.1039/c7ra07493j · Cited by 13 · see citing works
Near-IR aza-BODIPY-based probe for the selective simultaneous detection of Cu2+ in aqueous buffer solutions and its application in biological samples
Praikaew, P., Roongcharoen, T., Charoenpanich, A., Kungwan, N., & Wanichacheva, N. (2020) · Journal of Photochemistry and Photobiology A Chemistry · doi:10.1016/j.jphotochem.2020.112641 · Cited by 13 · see citing works
Excited State and Non-linear Optical Properties of NIR Absorbing β-Thiophene-Fused BF2-Azadipyrromethene Dyes—Computational Investigation
Gawale, Y., Rhyman, L., Elzagheid, M. I., Ramasami, P., & Sekar, N. (2017) · Journal of Fluorescence · doi:10.1007/s10895-017-2186-z · Cited by 12 · see citing works
Tailoring the Molecular Skeleton of Aza‐BODIPYs to Design Photostable Red‐Light‐Emitting Laser Dyes
Prieto‐Castañeda, A., Avellanal‐Zaballa, E., Gartzia‐Rivero, L., Cerdán, L., Agarrabeitia, A. R., García‐Moreno, I., Bañuelos, J., & Ortiz, M. J. (2018) · ChemPhotoChem · doi:10.1002/cptc.201800225 · Cited by 12 · see citing works
The impact of the heteroatom in a five-membered ring on the photophysical properties of difluoroborates
Grabarz, A. M., Jędrzejewska, B., Skotnicka, A., Murugan, N. A., Patalas, F., Bartkowiak, W., Jacquemin, D., & Ośmiałowski, B. (2019) · Dyes and Pigments · doi:10.1016/j.dyepig.2019.04.026 · Cited by 12 · see citing works
Synthesis and reactivity of aza-dipyrrin alkali metal salts
Diaz‐Rodriguez, R. M., Robertson, K. N., & Thompson, A. (2018) · Chemical Communications · doi:10.1039/c8cc07101b · Cited by 11 · see citing works
Red/NIR Thermally Activated Delayed Fluorescence from Aza‐BODIPYs
Avellanal‐Zaballa, E., Prieto‐Castañeda, A., García‐Garrido, F., Agarrabeitia, A. R., Rebollar, E., Bañuelos, J., García‐Moreno, I., & Ortiz, M. J. (2020) · Chemistry - A European Journal · doi:10.1002/chem.202002916 · Cited by 9 · see citing works
A Palette of Efficient and Stable Far-Red and NIR Dye Lasers
Avellanal‐Zaballa, E., Gartzia‐Rivero, L., Bañuelos, J., García‐Moreno, I., Agarrabeitia, A. R., Peña‐Cabrera, E., & Ortiz, M. J. (2020) · Applied Sciences · doi:10.3390/app10186206 · Cited by 10 · see citing works
Porphyrinoid macrocycles as potential photosensitizers for photodynamic inhibition of biofilm formation in household water storage systems
Malomane, N., Mlambo, M., Kuvarega, A. T., Moutloali, R. M., & Managa, M. (2024) · International Journal of Environmental Science and Technology · doi:10.1007/s13762-024-06065-x · Cited by 9 · see citing works
Enhanced in vivo Optical Imaging of the Inflammatory Response to Acute Liver Injury in C57BL/6 Mice Using a Highly Bright Near‐Infrared BODIPY Dye
Sirbu, D., Luli, S., Leslie, J., Oakley, F., & Benniston, A. C. (2019) · ChemMedChem · doi:10.1002/cmdc.201900181 · Cited by 9 · see citing works
Design and Synthesis of Far‐Red to Near‐Infrared Chromophores with Pyrazine‐Based Boron Complexes
Takahashi, H., Watanabe, H., Ito, S., Tanaka, K., & Chujo, Y. (2023) · Chemistry - An Asian Journal · doi:10.1002/asia.202300489 · Cited by 9 · see citing works
Understanding the effect of indole as a donor in fluorophores by the localization of acceptor
Jiang, K., Huang, Y., Wang, Z., Tian, X., Wu, A., Liang, W., & Liu, B. (2025) · Dyes and Pigments · doi:10.1016/j.dyepig.2025.112735 · Cited by 7 · see citing works
Design of Two‐Photon‐Excited Fluorescent Dyes Containing Fluoroborylene Groups
Zaleśny, R., Szczotka, N., Grabarz, A. M., Ośmiałowski, B., & Jacquemin, D. (2019) · ChemPhotoChem · doi:10.1002/cptc.201900084 · Cited by 7 · see citing works
Halogenated Bis(donor)‐aza‐BODIPY System for Inducing NIR Excitation: Effect of Thiophene and Aminophenyl Donors on Optical Properties and in vitro Tests for Breast Cancer
Rodríguez-Mayor, A. V., Rodriguez, M. A., Ramos‐Ortíz, G., Bañuelos‐Hernández, A. E., Pérez‐Hernández, N., & Santillan, R. L. (2025) · ChemistrySelect · doi:10.1002/slct.202406201 · Cited by 6 · see citing works
Aza-dipyrrinato ruthenium sensitizers for enhancement of Light-Harvesting ability of Dye-Sensitized solar cells
Shivaji, B. S., Swetha, T., Gayathri, T., & Singh, S. P. (2022) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2022.121131 · Cited by 6 · see citing works
Investigation of excited states of BODIPY derivatives and non-orthogonal dimers from the perspective of singlet fission
Goyal, S., & Reddy, S. R. (2024) · Physical Chemistry Chemical Physics · doi:10.1039/d4cp02656j · Cited by 5 · see citing works
Halogen bonding aza-BODIPYs for anion sensing and anion binding-modulated singlet oxygen generation
Taylor, A. J., & Beer, P. D. (2024) · Chemical Communications · doi:10.1039/d4cc02330g · Cited by 5 · see citing works
Data-driven discovery of organic electronic materials enabled by hybrid top-down/bottom-up designPreprint
Blaskovits, J. T., Laplaza, R., Vela, S., & Corminbœuf, C. (2022) · ChemRxiv · doi:10.26434/chemrxiv-2022-88t32 · Cited by 5 · see citing works
Fluorescent tamoxifen derivatives as biophotonic probes for the study of human breast cancer and estrogen-receptor directed photosensitizers
Díaz, M. L., Hernández, D., Valdés‐Baizabal, C., Lobo, F., Marín, R., Canerina‐Amaro, A., Boto, A., & Lahoz, F. J. (2023) · Optical Materials · doi:10.1016/j.optmat.2023.113736 · Cited by 3 · see citing works
Fast Synthesis of Tetra-Aryl-Substituted Aza-BODIPYs
Marfin, Y. S., Merkushev, D. A., & Khalabudin, D. (2021) · Journal of Physics Conference Series · doi:10.1088/1742-6596/1822/1/012004 · Cited by 2 · see citing works
Biomedical applications of AzaBODIPYs and their gold nanoparticle conjugates: The in vitro inhibition of Michigan Cancer Foundation-7 breast cancer cells
Molupe, N., Magwaza, T. M., Mack, J. P., & Nyokong, T. (2025) · Journal of Porphyrins and Phthalocyanines · doi:10.1142/s1088424625501135 · Cited by 1 · see citing works
CALCULATION GUIDED RATIONAL DESIGN AND SYNTHESIS OF NOVEL CATIONIC FLUORESCENT meso�PYRIDINIUM BODIPYS FOR BIO-IMAGING
LaMaster, D. J. (2018) · doi:10.31390/gradschool_dissertations.4762
Design, Synthesis, and Evaluation of Fluorogenic, BODIPY-based Probes for Specific Protein Labelling in Live Cells
Acton, S. L. (2019) · uO Research (University of Ottawa) · doi:10.20381/ruor-23282
Chemoselective nickel-catalyzed coupling through substrate photoexcitationPreprint
Das, P., Woods, E., Ly, J., Olding, J. N., Presley, K. F., Romanoff, B., Grusenmeyer, T. A., Weiss, E. A., & Kalow, J. A. (2021) · ChemRxiv · doi:10.26434/chemrxiv-2021-8wqv0
Controlling substrate selectivity in cross coupling with lightPreprint
Das, P., Woods, E., Ly, J., Olding, J. N., Presley, K. F., Romanoff, B., Grusenmeyer, T. A., Weiss, E. A., & Kalow, J. A. (2022) · ChemRxiv · doi:10.26434/chemrxiv-2021-8wqv0-v2
Contrast agent optimization for improved photoacoustic imaging
Bardon, K. M. (2023) · doi:10.17760/d20592710
Reactivity of an aza-dipyrrin and an aza-BODIPY motif bearing two 2-pyridyl units: an emissive NNN binding pocket
Gapare, R. L., Diaz‐Rodriguez, R. M., Williams, V. A., Atwood, M., Cotnam, M. J., Hilborn, J. W., Johnson, E. R., Robertson, K. N., & Thompson, A. (2025) · Organic & Biomolecular Chemistry · doi:10.1039/d5ob01628b
Selbstassemblierte (Aza‐)BODIPY Farbstoffe für Biomedizinische In Vivo Bildgebung
Albers, A., Masthoff, M., & Fernández, G. (2026) · Angewandte Chemie · doi:10.1002/ange.202525491
Aza-bodipy pour la limitation optique aux longueurs d'onde des télécommunications : synthèse des chromophores, optimisation de matériaux hybrides et études photophysiques
David, S. (2020) · doi:10.70675/79993519zaf26z4f79za76bz3bc7c39bdeb3
Donor engineering modulates the performance of D-π-A type aggregation-induced emission photosensitizers: a theoretical calculation study
Wang, W., Zhang, M., Sun, J., Ni, T., & Sun, J. (2026) · Structural Chemistry · doi:10.1007/s11224-026-02789-3
Photoactive NIR-Absorbing Aza-BODIPY Polymer Networks for High-Performance Supercapacitors
Özdemir, M., Çatoğlu, F., Altınışık, S., Köksoy, B., Yalcin, B., & Koyuncu, S. (2026) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.6c05842
A cheminformatics and DFT exploration of a brominated sulfonamide with nonlinear optical response and preliminary in silico bioactivity assessment
Neupane, B., Basnet, K., Ghimire, J., & Dhungel, S. K. (2026) · Molecular Diversity · doi:10.1007/s11030-026-11644-w
Impact of Intermolecular Charge Transfer Interaction on the Absorption Spectrum of an Aza-BODIPY Dye Aggregate
Bialas, D., Bialas, A. L., Hestand, N. J., & Zhang, K. (2026) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.6c03675
Recent advances in organic fluorescent dyes and responsive materials: from molecular design to functional biomedical applications
Mbugua, S. N. (2026) · Journal of Materials Chemistry B · doi:10.1039/d6tb01185c
Exploring Aza-BODIPY Derivatives as Sonosensitizers for Deep-Tissue Sonotheranostics in Breast Cancer
He, X., Zhao, M., Song, J., Li, J., Wang, J., Yao, P., Li, J., Wu, Z., Xu, Y., Zhai, T., et al. (2026) · ACS Applied Materials & Interfaces · doi:10.1021/acsami.6c14426

Synthesis, Structure, and Optical Studies of Donor–Acceptor‐Type Near‐Infrared (NIR) Aza–Boron‐Dipyrromethene (BODIPY) Dyes
Balsukuri, N., Lone, M. Y., Jha, P. C., Mori, S., & Gupta, I. (2016) · Chemistry - An Asian Journal · doi:10.1002/asia.201600167 · Cited by 49 · see citing works
Effect of the Aza-N-Bridge and Push–Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs
Schäfer, C., Mony, J., Olsson, T., & Börjesson, K. (2022) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.1c02525 · Cited by 27 · see citing works
Synthesis and optical properties of 1-ethyl-indol-3-yl-substituted aza-BODIPY dyes at the 1,7-positions
Loaeza, L., Corona‐Sánchez, R., Castro, G., Romero‐Ávila, M., Santillan, R. L., Maraval, V., Chauvin, R., & Farfán, N. (2021) · Tetrahedron · doi:10.1016/j.tet.2021.131983 · Cited by 7 · see citing works
Synthesis and properties of NIR aza-BODIPYs with aryl and alkynyl substituents on the boron center
Jiang, X., Fu, Y., Zhang, T., & Zhao, W. (2012) · Tetrahedron Letters · doi:10.1016/j.tetlet.2012.08.056 · Cited by 40 · see citing works
Photophysics and redox properties of aza-BODIPY dyes with electron-withdrawing groups
Gut, A., Łapok, Ł., Jamróz, D., Gorski, A., Solarski, J., & Nowakowska, M. (2017) · New Journal of Chemistry · doi:10.1039/c7nj02757e · Cited by 36 · see citing works

Authors: Karlsson, J. K. G., & Harriman, A.
Affiliations: Newcastle University (GB)
Corresponding author: Harriman, Anthony
ORCID: Karlsson, Joshua K. G.
Harriman, Anthony
Venue: The Journal of Physical Chemistry A
Publisher: American Chemical Society (ACS)
Published: 2016-04-18
Volume: 120
Issue: 16
Pages: 2537-2546
ISSN: 1089-5639 (ISSN-L)
1520-5215
DOI: 10.1021/acs.jpca.6b01278
OpenAlex: W2316983398
Cited by: 68
References: 72
Citations by year: 2026: 8 · 2025: 5 · 2024: 4 · 2023: 5 · 2022: 7 · 2021: 4 · 2020: 8 · 2019: 8 · 2018: 7 · 2017: 10 · 2016: 2
FWCI: 4.01
Type: journal article
Language: en
Open access: green
doi.org
Locations: The Journal of Physical Chemistry A (publishedVersion)
PubMed (publishedVersion)
Newcastle University ePrints (Newcastle Univesity)
Funders: Newcastle University
Topics: Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
Keywords: aza-BODIPY dyes, boron dipyrromethene, red shift, HOMO-LUMO gap, nonradiative decay, hydrogen bonding, triplet state, spin-orbit coupling, dihedral angle, π-electron delocalization, fluorescence, quantum chemical calculations

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Origin of the Red-Shifted Optical Spectra Recorded for Aza-BODIPY Dyes

Abstract

Integrity signals

Claims the paper makes

Claims other papers make about this one

Cites

Cited by

Related

Record

About these checks