Meso bromination and derivatization of synthetic bacteriochlorins

Jing, Haoyu; Liu, Sijia; Jiang, Jianbing; Tran, Vy-Phuong; Rong, Jie; Wang, Pengzhi; Lindsey, Jonathan S.

doi:10.1039/d1nj05853c

Meso bromination and derivatization of synthetic bacteriochlorins

Journal Article · Tue Mar 08 00:00:00 EST 2022 · New Journal of Chemistry

DOI:https://doi.org/10.1039/d1nj05853c· OSTI ID:1978809

Jing, Haoyu ^[1]; Liu, Sijia ^[2]; ^[2]; Tran, Vy-Phuong ^[2]; ^[2]; Wang, Pengzhi ^[2]; ^[2]

North Carolina State University, Raleigh, NC (United States); OSTI
North Carolina State University, Raleigh, NC (United States)

Here, the ability to prepare and tailor synthetic analogues of native bacteriochlorophylls enables diverse applications. A de novo route entails dimerization of a dihydrodipyrrin-acetal to afford the corresponding 5-methoxy and/or 5-unsubstituted bacteriochlorin, wherein each pyrroline ring contains a gem-dimethyl group to ensure stability toward adventitious dehydrogenation. The presence of a 5-methoxy group facilitates bromination at the distal meso-(15-)position. While bromination of 5-unsubstituted bacteriochlorins typically affords a mixture of brominated products, here the presence of two substitution patterns (2,12-dicarboethoxy, 2,12-diacetyl) has been found to facilitate selective meso-bromination in the absence of the methoxy substituent. The introduction of a single meso-bromine atom in a bacteriochlorin opens opportunities for Pd-mediated derivatization, which include (1) preparation of four ethynylphenyl building blocks (and two benchmark bacteriochlorins) with long-wavelength absorption bands tuned across 725–757 nm, for use in preparation of multichromophore arrays; (2) installation of a bioconjugatable group to free base bacteriochlorins or a copper bacteriochlorin, the latter for possible use in photoacoustic imaging; and (3) installation of an S-acetylthio group for surface attachment. Altogether, 25 new bacteriochlorins are described including 5 meso-bromobacteriochlorin intermediates and 12 target bacteriochlorins.

View Accepted Manuscript (DOE)

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

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

Grant/Contract Number:: FG02-05ER15661

OSTI ID:: 1978809

Alternate ID(s):: OSTI ID: 1853841

Journal Information:: New Journal of Chemistry, Journal Name: New Journal of Chemistry Journal Issue: 12 Vol. 46; ISSN NJCHE5; ISSN 1144-0546

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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