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Photoinduced electron transfer in porphyrin‐quinone cyclophanes, 6. Porphyrin‐quinone cyclophanes with gradually varied acceptor strength: Syntheses and characterizations
Author(s) -
Staab Heinz A.,
Weiser Jürgen,
Futscher Michael,
Voit Guido,
Rückemann Andreas,
Anders Christine
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921251017
Subject(s) - chemistry , cyclophane , porphyrin , quinone , photochemistry , intramolecular force , pyrrole , electron acceptor , electron transfer , condensation reaction , stereochemistry , crystallography , crystal structure , organic chemistry , catalysis
For studying intramolecular electron‐transfer reactions, three groups of double‐ and single‐bridged porphyrin‐quinone cyclophanes 1–4, 5–9 , and 11–14 , resp., with gradual variation of quinone acceptor strengths were synthesized. As key intermediates for building up the porphyrin‐cyclophane skeleton the correspondingly 3,6‐substituted 1,4‐bis[4‐(2‐formylphenyl)‐butyl]‐2,5‐dimethoxybenzenes 15–20 were synthesized. Condensation with pyrrole yielded the doubly bridged porphyrin cyclophanes 42–45 ; via the bis(dipyrrolylmethyl) derivatives 46–51 and 64–67 the single‐bridged porphyrin cyclophanes 58–63 and 72–75 were obtained by acidic condensation with triethyl formate. Cleavage of the methoxy groups and oxidation yielded the corresponding porphyrin‐quinone systems. Some magnesium and zinc complexes of these cyclophanes are described. Spectroscopic data (MS, 1 H NMR) are reported in support of the proposed structures.