Integration of Cyanine, Merocyanine and Styryl Dye Motifs with Synthetic Bacteriochlorins

Yang, Eunkyung; Zhang, Nuonuo; Krayer, Michael; Taniguchi, Masahiko; Diers, James R.; Kirmaier, Christine; Lindsey, Jonathan S.; Bocian, David F.; Holten, Dewey

doi:10.1111/php.12547

Title: Integration of Cyanine, Merocyanine and Styryl Dye Motifs with Synthetic Bacteriochlorins

Journal Article · Fri Dec 18 00:00:00 EST 2015 · Photochemistry and Photobiology

DOI:https://doi.org/10.1111/php.12547· OSTI ID:1401404

Yang, Eunkyung ^[1]; Zhang, Nuonuo ^[2]; Krayer, Michael ^[2]; Taniguchi, Masahiko ^[2]; Diers, James R. ^[3]; Kirmaier, Christine ^[1]; Lindsey, Jonathan S. ^[2]; Bocian, David F. ^[3]; Holten, Dewey ^[1]

Department of Chemistry Washington University St. Louis MO
Department of Chemistry North Carolina State University Raleigh NC
Department of Chemistry University of California Riverside CA

Abstract Understanding the effects of substituents on spectral properties is essential for the rational design of tailored bacteriochlorins for light‐harvesting and other applications. Toward this goal, three new bacteriochlorins containing previously unexplored conjugating substituents have been prepared and characterized. The conjugating substituents include two positively charged species, 2‐( N ‐ethyl 2‐quinolinium)vinyl‐ (B‐1) and 2‐( N ‐ethyl 4‐pyridinium)vinyl‐ (B‐2), and a neutral group, acroleinyl‐ (B‐3); the charged species resemble cyanine (or styryl) dye motifs whereas the neutral unit resembles a merocyanine dye motif. The three bacteriochlorins are examined by static and time‐resolved absorption and emission spectroscopy and density functional theoretical calculations. B‐1 and B‐2 have Q _y absorption bathochromically shifted well into the NIR region (822 and 852 nm), farther than B‐3 (793 nm) and other 3,13‐disubstituted bacteriochlorins studied previously. B‐1 and B‐2 have broad Q _y absorption and fluorescence features with large peak separation (Stokes shift), low fluorescence yields, and shortened S ₁ ( Q _y ) excited‐state lifetimes (~700 ps and ~100 ps). More typical spectra and S ₁ lifetime (~2.3 ns) are found for B‐3. The combined photophysical and molecular‐orbital characteristics suggest the altered spectra and enhanced nonradiative S ₁ decay of B‐1 and B‐2 derive from excited‐state configurations in which electron density is shifted between the macrocycle and the substituents.

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Sponsoring Organization:: USDOE

OSTI ID:: 1401404

Journal Information:: Photochemistry and Photobiology, Journal Name: Photochemistry and Photobiology Vol. 92 Journal Issue: 1; ISSN 0031-8655

Publisher:: Wiley-BlackwellCopyright Statement

Country of Publication:: United Kingdom

Language:: English

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Cited by: 6 works

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