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Cooperative C3‐ and C13‐Substituent Effects on Synthetic Chlorophyll Derivatives
Author(s) -
Sasaki Shinichi,
Yoshizato Mari,
Kunieda Michio,
Tamiaki Hitoshi
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000541
Subject(s) - chemistry , substituent , chlorin , deoxygenation , derivative (finance) , photochemistry , electrochemistry , medicinal chemistry , stereochemistry , porphyrin , organic chemistry , electrode , financial economics , economics , catalysis
C3‐vinyl and C13‐keto‐carbonyl groups of methyl pyropheophorbide‐ a , a chlorophyll‐ a derivative, were systematically modified to investigate the substituent effects along the y ‐axis of chlorin macrocycles. C13 1 deoxygenation resulted in blueshifts of the Q y absorption maxima and a large reduction of their redox potentials, whereas introduction of the dicyanomethylene group at the 13 1 ‐position caused the opposite effect on both optical and electrochemical properties. Among the nine chlorins examined, the Q y peak positions could be varied from 647 to 736 nm by the cooperative effects of the diagonal substituents' combinations.