Hydrophilic tetracarboxy bacteriochlorins for photonics applications

Jiang, Jianbing; Vairaprakash, Pothiappan; Reddy, Kanumuri Ramesh; Sahin, Tuba; Pavan, M. Phani; Lubian, Elisa; Lindsey, Jonathan S.

doi:10.1039/c3ob41791c

Hydrophilic tetracarboxy bacteriochlorins for photonics applications

Journal Article · Wed Jan 01 04:00:00 EST 2014 · Organic and Biomolecular Chemistry

DOI:https://doi.org/10.1039/c3ob41791c· OSTI ID:1097609

Jiang, Jianbing ^[1]; Vairaprakash, Pothiappan; Reddy, Kanumuri Ramesh; Sahin, Tuba; Pavan, M. Phani; Lubian, Elisa; Lindsey, Jonathan S.

Washington University

Bacteriochlorins absorb strongly in the near-infrared (NIR, 700–900 nm) region and hence are well suited for photophysical studies and photomedical applications, yet such endeavors heretofore have been largely limited by the intrinsic lipophilicity of the bacteriochlorin macrocycle. Here, a new molecular design is investigated wherein 3,5-dicarboxyphenyl units are appended to the β-pyrrolic positions of the bacteriochlorin. Use of the 3,5-aryl substitution motif places the carboxylic acid groups, which are anionic at neutral pH, above and below the plane of the bacteriochlorin macrocycle. A de novo synthesis has been employed to create five such bacteriochlorins, which uses as intermediates two new 2,12-dibromobacteriochlorin building blocks and a known 3,13-dibromobacteriochlorin. The aryl groups with protected carboxylate moieties were introduced by Suzuki coupling; subsequent deprotection afforded the hydrophilic bacteriochlorins. The latter were characterized by absorption and fluorescence spectroscopy in DMF and in aqueous phosphate buffer (pH 7).

Research Organization:: Washington Univ., St. Louis, MO (United States); Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001035

OSTI ID:: 1097609

Report Number(s):: DE-SC0001035-93

Journal Information:: Organic and Biomolecular Chemistry, Journal Name: Organic and Biomolecular Chemistry Journal Issue: 1 Vol. 12; ISSN 1477-0520

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

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