Effects of Strong Electronic Coupling in Chlorin and Bacteriochlorin Dyads

Kang, Hyun Suk; Esemoto, Nopondo N.; Diers, James R.; Niedzwiedzki, Dariusz M.; Greco, Jordan A.; Akhigbe, Joshua; Yu, Zhanqian; Pancholi, Chirag; Bhagavathy, Ganga Viswanathan; Nguyen, Jamie K.; Kirmaier, Christine; Birge, Robert R.; Ptaszek, Marcin; Holten, Dewey; Bocian, David F.

doi:10.1021/acs.jpca.5b10686

Effects of Strong Electronic Coupling in Chlorin and Bacteriochlorin Dyads

Journal Article · Thu Jan 14 00:00:00 EST 2016 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.5b10686· OSTI ID:1774949

Kang, Hyun Suk ^[1]; Esemoto, Nopondo N. ^[2]; Diers, James R. ^[3]; Niedzwiedzki, Dariusz M. ^[4]; Greco, Jordan A. ^[5]; Akhigbe, Joshua ^[2]; Yu, Zhanqian ^[2]; Pancholi, Chirag ^[2]; Bhagavathy, Ganga Viswanathan ^[2]; Nguyen, Jamie K. ^[2]; Kirmaier, Christine ^[4]; Birge, Robert R. ^[5]; Ptaszek, Marcin ^[2]; Holten, Dewey ^[4]; Bocian, David F. ^[3]

Washington Univ., St. Louis, MO (United States); Washington University
Univ. of Maryland Baltimore County (UMBC), Baltimore, MD (United States)
Univ. of California, Riverside, CA (United States)
Washington Univ., St. Louis, MO (United States)
Univ. of Connecticut, Storrs, CT (United States)

Achieving tunable, intense near-infrared absorption in molecular architectures with properties suitable for solar light harvesting and biomedical studies is of fundamental interest. Herein, we report the photophysical, redox, and molecular-orbital characteristics of nine hydroporphyrin dyads and associated benchmark monomers that have been designed and synthesized to attain enhanced light harvesting. Each dyad contains two identical hydroporphyrins (chlorin or bacteriochlorin) connected by a linker (ethynyl or butadiynyl) at the macrocycle β-pyrrole (3- or 13-) or meso (15-) positions. The strong electronic communication between constituent chromophores is indicated by the doubling of prominent absorption features, split redox waves, and paired linear combinations of frontier molecular orbitals. Relative to the benchmarks, the chlorin dyads in toluene show substantial bathochromic shifts of the long-wavelength absorption band (17-31 nm), modestly reduced singlet excited-state lifetimes (τ_S = 3.6-6.2 ns vs 8.8-12.3 ns), and increased fluorescence quantum yields (Φ_f = 0.37-0.57 vs 0.34-0.39). The bacteriochlorin dyads in toluene show significant bathochromic shifts (25-57 nm) and modestly reduced τ_S (1.6-3.4 ns vs 3.5-5.3 ns) and Φ_f (0.09-0.19 vs 0.17-0.21) values. The τ_S and Φ_f values for the bacteriochlorin dyads are reduced substantially (up to ~20-fold) in benzonitrile. The quenching is due primarily to the increased S₁ → S_o internal conversion that is likely induced by increased contribution of charge-resonance configurations to the S₁ excited state in the polar medium. Lastly, the fundamental insights gained on the physicochemical properties of the strongly coupled hydroporphyrin dyads may aid utilization in solar-energy conversion and photomedical research.

View Accepted Manuscript (DOE)

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

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

Grant/Contract Number:: FG02-05ER15660; FG02-05ER15661

OSTI ID:: 1774949

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 3 Vol. 120; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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