Journal
ORGANIC LETTERS
Volume 13, Issue 9, Pages 2380-2383Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2006264
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- U.S. National Science Foundation [CHEM-0517782]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1048717] Funding Source: National Science Foundation
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Alkyl-Grignard addition to meso-tetraphenylporpholactone generates monoalkyl- and gem-bis-alkyloxazolochlorins. Together with compounds made by further synthetic manipulations of these derivatives, a series of chlorin-type chromophores with modulated optical properties is generated. Furthermore, their OsO4-mediated dihydroxylations and subsequent functional group transformations generate a family of bacteriochlorins that possess substituent-dependent optical properties. Thus, the formal replacement of a pyrrolidine moiety in chlorins and bacteriochlorins by variously substituted oxazoles is a flexible methodology to generate novel and stable chromophores that are tunable over a considerable range of the optical spectrum.
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