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Synthesis of New Pyropheophytin-naphthoquinone Dyads for Investigations of Photoinduced Electron Transfer

✍ Scribed by Malinen, Pasi K. ;Tauber, Andrei Y. ;Helaja, Juho ;Hynninen, Paavo H.

Book ID
102366009
Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
415 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Two new, covalently‐linked pyropheophytin‐naphthoquinone dyads 1 and 2 have been synthesized for use as model compounds in studies of photoinduced electron transfer. The starting material for the synthesis was chlorophyll a (3). This was first pyrolyzed to 13^2^‐demethoxycarbonylchlorophyll a (4), which was then oxidized regioselectively to 13^2^‐demethoxycarbonyl‐P4(R/S)‐hydroxypheophytin a (5). Compound 5 was esterified with naphthoquinone carboxylic acid 17 by the carbodiimide method to afford 13^2^‐demethoxycarbonyl‐P4(R/S)‐oxy‐[2‐(2′‐carboxyethyl)‐3‐methyl‐1,4‐naphthoquinone]pheophytin a (1) and (2). The observation that fluorescence emission is effectively quenched in dyads 1 and 2, relative to compound 5 which does not bear an electron‐acceptor, indicates that intramolecular electron transfer from the excited donor part to the ground state acceptor part of the molecule occurs readily.

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