Tunable meso-Tetraphenyl-alkyloxazolo-chlorins and -bacteriochlorins † Oxazolochlorins 4. Oxazolochlorins 3: Khalil, G. E.; Daddario, P.; Lau, K. S. F.; Imtiaz, S.; King, M.; Gouterman, M.; Sidelev, A.; Ghandehari, M.; Brückner, C. Analyst 2010, 135, 2125−2131

• Published in: Organic letters 2011-05, Vol.13 (9), p.2380-2383
• Main Authors: Ogikubo, Junichi, Brückner, Christian
• Format: Article
• Language: English
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol2006264

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.