Synthesis of Helically π‐Extended N‐Confused Porphyrin Dimer via meso‐Bipyrrole‐Bridge with Near‐Infrared‐II Absorption Capability
Abstract
Quinoidal dimeric porphyrin dye synthesis exhibiting second near‐infrared (NIR‐II) absorbability is described herein. A precisely designed meso‐pyrrolyl‐substituted N‐confused porphyrin possesses a distinct metal coordination site at the periphery. Nickel metalation of this compound led to the oxidative C−H coupling between adjacent α‐pyrrole rings, affording two dimeric complexes, which exhibited intense NIR‐II absorptions ranging from 1000 to 1400 nm. As was evidenced by decreased aromaticity, the quinoidal resonant structures contributed to the emergence of photoacoustic spectral capabilities in the NIR‐II window. Thus, the potential of these compounds as prototypical contrast agents in various bioimaging applications has been demonstrated.
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Furuta et al. demonstrated that metal-directed assembly of porphyrinoid dimers can achieve NIR-II absorption.
“Furuta et al.193 demonstrated that metal-directed assembly of porphyrinoid dimers can also achieve NIR-II absorption.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
In the presence of Ni(II) salts, a metal-directed oxidative C-C coupling reaction linked the meso-pyrrolic α-positions, producing Ni(II)-coordinated NCP dimers (7Ni) with a helical π-extended framework.
“In the presence of Ni(II) salts, a metal-directed oxidative C-C coupling reaction linked the meso-pyrrolic α-positions, producing Ni(II)-coordinated NCP dimers (7Ni) with a helical π-extended framework.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
Another dimer (8Ni) displayed an even stronger absorption band at 1037 nm.
“Another dimer (8Ni) displayed an even stronger absorption band at 1037 nm.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
UV-Vis-NIR characterization revealed a split Soret band (446 and 562 nm) and a dramatically red-shifted Q-like band at 1262 nm (with a tail to 1400 nm) compared to the monomer (6).
“Ultraviolet–Visible–Near-Infrared (UV–Vis–NIR) characterization revealed a split Soret band (446 and 562 nm) and a dramatically red-shifted Q-like band at 1262 nm (with a tail to 1400 nm) compared to the monomer (6).”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
Their design employed a precisely modified N-confused porphyrin (NCP) unit providing peripheral metal-coordination sites.
“Their design employed a precisely modified N-confused porphyrin (NCP) unit providing peripheral metal-coordination sites.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
Biomedical application of metal complexes is hindered by a reliance on high-energy, short-wavelength excitation, leading to phototoxicity and poor tissue penetration.
“Nevertheless, their biomedical application is hindered by a reliance on high-energy, short-wavelength excitation, which leads to phototoxicity and poor tissue penetration.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
Metal complexes are promising photofunctional materials due to superior photostability, large Stokes shifts, and high emission quantum yields compared to organic chromophores.
“Metal complexes are promising photofunctional materials due to their superior photostability, large Stokes shifts, and high emission quantum yields compared to organic chromophores”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [193]
Cites
Geuenich, D., Hess, K., Köhler, F., & Herges, R. (2005) · Chemical Reviews · doi:10.1021/cr0300901 · Cited by 1,675 · see citing works
Structural Aspects of Aromaticity
Krygowski, T. M., & Cyrański, M. K. (2001) · Chemical Reviews · doi:10.1021/cr990326u · Cited by 1,410 · see citing works
Conjugated porphyrin arrays: synthesis, properties and applications for functional materials
Tanaka, T., & Osuka, A. (2014) · Chemical Society Reviews · doi:10.1039/c3cs60443h · Cited by 702 · see citing works
"N-Confused Porphyrin": A New Isomer of Tetraphenylporphyrin
Furuta, H., Asano, T., & Ogawa, T. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00081a047 · Cited by 698 · see citing works
Self-citationTetra‐p‐tolylporphyrin with an Inverted Pyrrole Ring: A Novel Isomer of Porphyrin
Chmielewski, P. J., Latos‐Grażyński, L., Rachlewicz, K., et al. (1994) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199407791 · Cited by 641 · see citing works
Building molecular wires from the colours of life: conjugated porphyrin oligomers
Anderson, H. L. (1999) · Chemical Communications · doi:10.1039/a904209a · Cited by 559 · see citing works
Recent advances in near-infrared II fluorophores for multifunctional biomedical imaging
Ding, F., Zhan, Y., Lu, X., & Sun, Y. (2018) · Chemical Science · doi:10.1039/c8sc01153b · Cited by 540 · see citing works
Near Infrared (NIR) absorbing dyes as promising photosensitizer for photo dynamic therapy
Chinna Ayya Swamy, P., Sivaraman, G., Priyanka, R. N., Raja, S. O., Ponnuvel, K., Shanmugpriya, J., & Gulyani, A. (2020) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2020.213233 · Cited by 304 · see citing works
de la Torre, G., Bottari, G., Sekita, M., Hausmann, A., Guldi, D. M., & Torres⊗, T. (2013) · Chemical Society Reviews · doi:10.1039/c3cs60140d · Cited by 193 · see citing works
NH Tautomerism of N-Confused Porphyrin
Furuta, H., Ishizuka, T., Osuka, A., et al. (2001) · Journal of the American Chemical Society · doi:10.1021/ja010237a · Cited by 174 · see citing works
Self-citationMonoinvertiertes Tetra‐p‐tolylporphyrin: ein neues Porphyrinisomer
Chmielewski, P. J., Latos‐Grażyński, L., Rachlewicz, K., et al. (1994) · Angewandte Chemie · doi:10.1002/ange.19941060721 · Cited by 161 · see citing works
Tris(pyrazolyl)methanesulfonates: A Novel Class of Water-Soluble Ligands
Kläui, W., Berghahn, M., Rheinwald, G., & Lang, H. (2000) · Angewandte Chemie International Edition · doi:10.1002/1521-3773(20000717)39:14 · Cited by 126 · see citing works
Nanoparticles of Chlorin Dimer with Enhanced Absorbance for Photoacoustic Imaging and Phototherapy
Zheng, X., Wang, L., Liu, S., et al. (2018) · Advanced Functional Materials · doi:10.1002/adfm.201706507 · Cited by 115 · see citing works
Photoacoustic imaging and photothermal therapy in the second near-infrared window
Ge, X., Fu, Q., Bai, L. L., et al. (2019) · New Journal of Chemistry · doi:10.1039/c9nj01402k · Cited by 99 · see citing works
Theoretical Study of Stability, Structures, and Aromaticity of Multiply N-Confused Porphyrins
Furuta, H., Maeda, H., & Osuka, A. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo016051b · Cited by 85 · see citing works
Self-citationTanaka, T., & Osuka, A. (2018) · Chemistry - A European Journal · doi:10.1002/chem.201802810 · Cited by 76 · see citing works
Thorley, K. J., Hales, J. M., Anderson, H. L., et al. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802687 · Cited by 75 · see citing works
Synthesis and Characterization of a Directly Linked N‐Confused Porphyrin Dimer
Chmielewski, P. J. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200461361 · Cited by 73 · see citing works
Shimomura, K., Kai, H., Nakamura, Y., Hong, Y., Mori, S., Miki, K., Ohe, K., Notsuka, Y., Yamaoka, Y., Ishida, M., et al. (2020) · Journal of the American Chemical Society · doi:10.1021/jacs.9b13475 · Cited by 67 · see citing works
Self-citationWang, Y., Kai, H., Ishida, M., Gokulnath, S., Mori, S., Murayama, T., Muranaka, A., Uchiyama, M., Yasutake, Y., Fukatsu, S., et al. (2020) · Journal of the American Chemical Society · doi:10.1021/jacs.0c01824 · Cited by 67 · see citing works
Self-citationGill, H. S., Finger, I., Božidarević, I., et al. (2005) · New Journal of Chemistry · doi:10.1039/b412620c · Cited by 60 · see citing works
Quinone-fused porphyrins as contrast agents for photoacoustic imaging
Banala, S., Fokong, S., Brand, C., Andreou, C., Kräutler, B., Rueping, M., & Kiessling, F. M. (2017) · Chemical Science · doi:10.1039/c7sc01369h · Cited by 58 · see citing works
Inverted N‐Confused Porphyrin Dimer
Ishizuka, T., Osuka, A., & Furuta, H. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200460017 · Cited by 53 · see citing works
Self-citationSynthesis and Characterization of a Directly Linked N‐Confused Porphyrin Dimer
Chmielewski, P. J. (2004) · Angewandte Chemie · doi:10.1002/ange.200461361 · Cited by 44 · see citing works
Saltsman, I., Goldberg, I., Balasz, Y., et al. (2006) · Tetrahedron Letters · doi:10.1016/j.tetlet.2006.11.052 · Cited by 42 · see citing works
Fukui, N., & Osuka, A. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201802494 · Cited by 37 · see citing works
Pyrrole chemistry. XXII. A "one-pot" synthesis of some 4-acylpyrrole-2-carboxaldehydes from pyrrole
Anderson, H. J., Loader, C. E., & Poster, A. (1980) · Canadian Journal of Chemistry · doi:10.1139/v80-404 · Cited by 35 · see citing works
Organic electroluminescent materials and devices emitting in UV and NIR regions
Pushkarev, A. P., & Bochkarev, M. N. (2016) · Russian Chemical Reviews · doi:10.1070/rcr4665 · Cited by 35 · see citing works
Chmielewski, P. J., Durlej, B., Siczek, M., et al. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904289 · Cited by 33 · see citing works
Tris(pyrazolyl)methansulfonate: eine neue Klasse wasserlöslicher Liganden
Kläui, W., Berghahn, M., Rheinwald, G., & Lang, H. (2000) · Angewandte Chemie · doi:10.1002/1521-3757(20000717)112:14 · Cited by 32 · see citing works
Cho, S. J., Yoon, M., Kim, C. H., et al. (2007) · The Journal of Physical Chemistry C · doi:10.1021/jp068522+ · Cited by 31 · see citing works
Enantiomer Resolution of Intrinsically Chiral C21‐Alkylated N‐Confused Porphyrin Complexes
Chmielewski, P. J., Szterenberg, L., & Siczek, M. (2010) · Chemistry - A European Journal · doi:10.1002/chem.201000534 · Cited by 29 · see citing works
Dipyrrin‐Bis(N‐Confused Porphyrin) Conjugate: Synthesis, Synergetic Ligation and Chirality Sensing
Wojaczyński, J., Maciołek, J., & Chmielewski, P. J. (2017) · Chemistry - An Asian Journal · doi:10.1002/asia.201700129 · Cited by 27 · see citing works
Photoacoustic Imaging Probes Based on Tetrapyrroles and Related Compounds
Merkes, J. M., Zhu, L., Bahukhandi, S. B., Rueping, M., Kiessling, F. M., & Banala, S. (2020) · International Journal of Molecular Sciences · doi:10.3390/ijms21093082 · Cited by 25 · see citing works
Li, C., Zhu, L., Liang, W., Su, R., Yin, J., Hu, Y., Lan, Y., Wu, D., & You, J. (2019) · Chemical Science · doi:10.1039/c9sc01596e · Cited by 24 · see citing works
Fujimoto, K., & Osuka, A. (2018) · Chemistry - A European Journal · doi:10.1002/chem.201800854 · Cited by 20 · see citing works
Jiblaoui, A., Baudequin, C., Chaleix, V., et al. (2013) · Tetrahedron · doi:10.1016/j.tet.2013.04.092 · Cited by 19 · see citing works
Synthesis and Properties of Acetylene-bridged N-Confused Porphyrin Dimers
Toganoh, M., Takayama, T., Nandy, R., et al. (2011) · Chemistry Letters · doi:10.1246/cl.2011.1021 · Cited by 18 · see citing works
Thorley, K. J., Hales, J. M., Anderson, H. L., et al. (2008) · Angewandte Chemie · doi:10.1002/ange.200802687 · Cited by 17 · see citing works
meso-to-meso 2,5-Pyrrolylene bridged zig-zag porphyrin arrays
Zhang, S., Kim, J., Li, Y., et al. (2017) · Chemical Communications · doi:10.1039/c7cc06793c · Cited by 16 · see citing works
Fukui, N., & Osuka, A. (2018) · Angewandte Chemie · doi:10.1002/ange.201802494 · Cited by 11 · see citing works
Inverted N‐Confused Porphyrin Dimer
Ishizuka, T., Osuka, A., & Furuta, H. (2004) · Angewandte Chemie · doi:10.1002/ange.200460017 · Cited by 10 · see citing works
Self-citationChmielewski, P. J., Durlej, B., Siczek, M., et al. (2009) · Angewandte Chemie · doi:10.1002/ange.200904289 · Cited by 10 · see citing works
2,6-/1,5-Naphthoquinodimethane bridged porphyrin dimer diradicaloids
Zhang, H.-J., Kim, J., Phan, H., Herng, T., Gopalakrishna, T. Y., Zeng, W.-D., Ding, J., Kim, D., & Wu, J.-S. (2020) · Journal of Porphyrins and Phthalocyanines · doi:10.1142/s1088424619500998 · Cited by 6 · see citing works
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Organic small-molecule NIR-II fluorophores for tumor phototheranostics
Xiang, D., Wang, Z., Zheng, H., Tang, Y., & Li, Q. (2026) · Light: Science & Applications · doi:10.1038/s41377-026-02212-w · Cited by 22 · see citing works
“13 and Table 6) 193 – 199 .”
- Authors
- Yamasumi, K., Notsuka, Y., Yamaoka, Y., Mori, S., Ishida, M., & Furuta, H.
- Affiliations
- Kyushu University (JP)
- Saga University (JP)
- Ehime University (JP)
- Corresponding author
- Ishida, Masatoshi
- Furuta, Hiroyuki
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2020-10-04
- Volume
- 26
- Issue
- 60
- Pages
- 13590-13594
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W3033219150
- Cited by
- 28
- References
- 44
- Citations by year
- 2026: 4 · 2025: 5 · 2024: 3 · 2023: 5 · 2022: 6 · 2021: 5
- FWCI
- 1.55
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemistry - A European Journal (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Japan Society for the Promotion of Science (JP19K05439, JP19H04586, JP20H00406)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Keywords
- N-confused porphyrin, porphyrin dimers, photoacoustic imaging, aromaticity
- MeSH terms
- Metals, Nickel, Porphyrins, Pyrroles, Spectrophotometry, Infrared, Coordination Complexes
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