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Synthesis of a chlorophyll-a derivative fused with an additional exo-five-membered ring and its optical properties

Author:
Doi, Marie, Tamiaki, Hitoshi
Source:
Tetrahedron letters 2019 v.60 no.33 pp. 150934
ISSN:
0040-4039
Subject:
absorption, bromination, chlorophyll, ethylene, methylene chloride, moieties, optical properties, wavelengths
Abstract:
A C20-free chlorophyll-a derivative with an additional exo-five-membered ring was successfully prepared using an ethylene linkage at the C3- and C5-positions. A bromination at the C20-position was requisite for the cyclization of a 1-hydroxyethyl or vinyl group at the C3-position of methyl bacteriopheophorbide-d or methyl pyropheophorbide-a, respectively. By comparing optical properties of the cyclized product with those of its 3-ethyl uncyclized analog in a diluted dichloromethane solution, it was shown that the cyclization shifted the Qx and Bx absorption maxima to longer wavelengths and reduced the Stokes shift.
Agid:
6536677