Beyond green with synthetic chlorophylls – Connecting structural features with spectral properties

Taniguchi, Masahiko; Bocian, David F.; Holten, Dewey; Lindsey, Jonathan S.

doi:10.1016/j.jphotochemrev.2022.100513

Beyond green with synthetic chlorophylls – Connecting structural features with spectral properties

Journal Article · Fri Mar 25 00:00:00 EDT 2022 · Journal of Photochemistry and Photobiology C: Photochemistry Reviews

DOI:https://doi.org/10.1016/j.jphotochemrev.2022.100513· OSTI ID:1977387

Taniguchi, Masahiko ^[1]; Bocian, David F. ^[2]; Holten, Dewey ^[3]; Lindsey, Jonathan S. ^[4]

North Carolina State University, Raleigh, NC (United States); OSTI
Univ. of California, Riverside, CA (United States)
Washington Univ., St. Louis, MO (United States)
North Carolina State University, Raleigh, NC (United States)

The distinct features of chlorophylls in photosynthesis have led to the formation of numerous derivatives for applications encompassing solar energy conversion, molecular photonics, photodynamic therapy, and molecular imaging. Synthetic chlorins created de novo and bearing a geminal dimethyl group in the reduced ring have proved invaluable for fundamental studies. Four decades of research have led to accumulation of tabulated spectra for > 400 such synthetic chlorins with distinct structural frameworks (17-oxochlorins, 13¹-oxophorbines, chlorinimides) and substituents (alkyl, aryl, ethynyl, phenylethynyl, acetyl, formyl) located at specific (meso, β) positions. In this review, spectral traces (324 absorption, 247 fluorescence) are assembled along with photophysical data including the molar absorption coefficient (ε), fluorescence quantum yield (Φ_f) and singlet excited-state lifetime (τ_s). The review uses the accumulated spectral data derived from chlorins all containing a uniform molecular scaffold to (1) highlight the effects of molecular structure on spectral features, and (2) identify trends including how ε, Φ_f and τ_s vary with wavelength and other features. Use of a common geminal-dimethyl-substituted chlorin scaffold – beginning with no substituents, to one substituent at designated sites, and to 2 or more substituents – provides a systematic Aufbau approach for understanding the absorption spectra of chlorins on a path to and beyond the native chlorophylls. Finally, the review provides insights concerning the rational design of potent analogues of Nature’s preeminent red-region absorbers for potential utilization in diverse applications and is aimed at multiple audiences: those interested in spectral properties, tetrapyrrole photophysics, and the molecular design of new chromophores.

View Accepted Manuscript (DOE)

Research Organization:: Washington Univ., St. Louis, MO (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: FG02-05ER15661

OSTI ID:: 1977387

Alternate ID(s):: OSTI ID: 1875583

Journal Information:: Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Journal Name: Journal of Photochemistry and Photobiology C: Photochemistry Reviews Journal Issue: C Vol. 52; ISSN 1389-5567

Publisher:: Japanese Photochemistry Association - ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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