Solid‐State Emission from Mono‐ and Bichromophoric Boron Dipyrromethene (BODIPY) Derivatives and Comparison with Fluid Solution
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The syntheses and crystal structures of sterically crowded mono‐ and bichromophoric BODIPY‐based dyes are reported. The “monomeric” compound is weakly fluorescent in the liquid phase due to fast internal conversion associated with rotation of aryl rings at the boron atom. The side‐by‐side “dimer” exhibits weak excitonic coupling between the dipyrrin units and is much more emissive in fluid solution. Solid samples of both molecular entities are strongly fluorescent under near‐UV illumination. Thus, the mono‐chromophore exhibits dual fluorescence from what appears to be a mixture of crystalline and possibly amorphous (or interfacial regions) distributions. The bi‐chromophore packs in the crystal as pairs of chromophores with each unit being provided by a different molecule. This leads to excitonic splitting and the formation of a strong H‐band in the absorption spectrum. Fluorescence occurs from the corresponding J‐species and also from what appears to be an aggregated state associated with interfacial areas. Both bulk and interface‐bound states show relatively long‐lived fluorescence while the crystal structures indicate the likelihood for fast electronic energy migration between molecules.
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The amorphous aggregate domains that act as excitation traps for J-aggregates were observed in BODIPY-based nanomaterials.
“The amorphous aggregate domains that act as excitation traps for J-aggregates were observed in BODIPY-based nanomaterials.”
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 [125]
The presence of such amorphous domains at an interface with the ordered crystalline J-aggregate columns promotes energy transfer from the crystalline phase to the amorphous phase, with subsequent fluorescence from the weakly emissive more red-shifted aggregates.
“The presence of such amorphous domains at an interface with the ordered crystalline J-aggregate columns promotes energy transfer from the crystalline phase to the amorphous phase, with subsequent fluorescence from the weakly emissive more red-shifted aggregates (Figure 5c).125”
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 [125]
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Self-citationSynthesis of multi-branched dipyrromethene dyes with soluble diethynylphenyl links
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Solvent relaxation of oxazine-4 in 2-methyltetrahydrofuran
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Synthesis of carbazole-based BODIPY dimers showing red fluorescence in the solid state
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Electronic Communication in Closely Connected BODIPY-Based Bichromophores
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Self-citationYamane, H., Ito, S., Tanaka, K., & Chujo, Y. (2016) · Polymer Chemistry · doi:10.1039/c6py00377j · Cited by 24 · see citing works
Energy harvesting: a review of the interplay between structure and mechanism
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Excitonic Coupling in Acyclic and Cyclic Dithioaryl‐Linked BODIPY DYEmers
Ahrens, J., Scheja, A., Wicht, R., & Bröring, M. (2016) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201600359 · Cited by 23 · see citing works
Jiang, L., Gao, H., Gai, L., & Shen, Z. (2018) · New Journal of Chemistry · doi:10.1039/c8nj00031j · Cited by 23 · see citing works
Liu, Y., Niu, L., Liu, X., Chen, P., Yao, Y., Chen, Y., & Yang, Q. (2018) · Chemistry - A European Journal · doi:10.1002/chem.201802157 · Cited by 22 · see citing works
Li, T., Gu, W., Yu, C., Lv, X., Wang, H., Hao, E., & Jiao, L. (2016) · Chinese Journal of Chemistry · doi:10.1002/cjoc.201600500 · Cited by 18 · see citing works
Paitandi, R. P., Singh, R. S., Dwivedi, B. K., Singh, V. D., & Pandey, D. S. (2018) · Dalton Transactions · doi:10.1039/c7dt04047d · Cited by 18 · see citing works
Solid-state emissive O-BODIPY dyes with bimodal emissions across red and near infrared region
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Self-citationAl‐Aqar, R., Benniston, A. C., Harriman, A., & Perks, T. (2016) · ChemPhotoChem · doi:10.1002/cptc.201600016 · Cited by 17 · see citing works
Self-citationSinglet Excitation Transfer in Columnar Liquid Crystals Studied by Monte Carlo Simulations
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Synthesis and Properties of a Covalently Linked Angular Perylene Imide Dimer
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Nonradiative Decay Channels for a Structurally-Distorted, Monostrapped BODIPY Derivative
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Self-citationLeushina, E., Usol'tsev, I. A., Bezzubov, S. I., Moiseeva, A. A., Terenina, M. V., Anisimov, A. V., Taydakov, I. V., & Khoroshutin, A. V. (2017) · Dalton Transactions · doi:10.1039/c7dt03801a · Cited by 6 · see citing works
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Self-citationFluorescence Spectroscopy of AdamBODIPY Single Crystals
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BODIPY-Based Molecules, a Platform for Photonic and Solar Cells
Squeo, B. M., Ganzer, L., Virgili, T., & Pasini, M. (2020) · Molecules · doi:10.3390/molecules26010153 · Cited by 96 · see citing works
“[89] studying the emission variation related to different distributions of crystalline and amorphous regions while the range of states produced by system self-assembly (from extended aggregates to other different structures) and influenced by side-group structure was investigated by Musser et al.”
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Self-reporting heavy atom-free photodynamic therapy agents
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Recent Advances in Boron-Containing Materials
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Origin of Fluorescence from Boranils in the Crystalline Phase
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Self-citationSynthesis, optical and electrochemical properties of propeller-type 3,5,8-trithienyl-BODIPY dyes
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Caging of Bodipy Photosensitizers through Hydrazone Bond Formation and their Activation Dynamics
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Self-citationSolid-state host–guest influences on a BODIPY dye hosted within a crystalline sponge
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Triplet Distribution in a Symmetrical Zinc(II) Porphyrin–BODIPY Pentameric Array
Bozdemir, Ö. A., Gültekin, D. D., & Harriman, A. (2020) · The Journal of Physical Chemistry A · doi:10.1021/acs.jpca.0c09243 · Cited by 8 · see citing works
Self-citationShahu, A., Petropoulos, V., Saridakis, E., Petrakis, V. S., Ioannidis, N. E., Mitrikas, G., Schiza, A., Chochos, C. L., Kasimati, E.-M., Soultati, A., et al. (2024) · Journal of the American Chemical Society · doi:10.1021/jacs.4c02019 · Cited by 6 · see citing works
Chinta, R. V. R. N., Sulava, S., Aradhyula, B. P. R., Jandhyam, H., Alone, D. P., & Venkatasubbaiah, K. (2023) · New Journal of Chemistry · doi:10.1039/d3nj02622a · Cited by 6 · see citing works
Kojima, Y., Sugiura, S., Suzuki, K., Yisilamu, Y., & Ono, K. (2021) · Chemistry - An Asian Journal · doi:10.1002/asia.202101262 · Cited by 5 · see citing works
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Sherudillo, A. S., Antina, L. A., Lukanov, M. M., Ksenofontov, A. A., Dyshin, A. A., Kiselev, M. G., Березин, М. Б., & Antina, E. V. (2024) · Journal of Molecular Liquids · doi:10.1016/j.molliq.2024.126812 · Cited by 1 · see citing works
Stereochemical Control of Secondary Benzamide‐based BODIPY Emitters
Waly, S. M. A., Benniston, A. C., Karlsson, J. K. G., Dixon, C., Wills, C., Waddell, P. G., & Harriman, A. (2023) · Chemistry - A European Journal · doi:10.1002/chem.202300383 · Cited by 1 · see citing works
Self-citationBio-Inspired Artificial Light-Harvesting Arrays Based on Boron(III)-Chelates
Al‐Sharif, H. H. T., & Harriman, A. (2020) · IntechOpen eBooks · doi:10.5772/intechopen.91853
Self-citation
- Authors
- Bozdemir, Ö. A., Al‐Sharif, H. H. T., McFarlane, W., Waddell, P. G., Benniston, A. C., & Harriman, A.
- Affiliations
- Atatürk University (TR)
- Newcastle University (GB)
- Corresponding author
- Harriman, Anthony
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2019-11-07
- Volume
- 25
- Issue
- 68
- Pages
- 15634-15645
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2978492934
- Cited by
- 20
- References
- 133
- Citations by year
- 2024: 4 · 2023: 3 · 2022: 4 · 2021: 1 · 2020: 7 · 2019: 1
- FWCI
- 1.17
- Type
- journal article
- Language
- en
- Open access
- green
- doi.org
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- Newcastle University ePrints (Newcastle Univesity)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Keywords
- boron dipyrromethene, BODIPY dyes, solid-state fluorescence, crystal packing, excitonic coupling, H-band, J-aggregates, interfacial states, internal rotation, chromophore dimers, amorphous regions
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