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Porphyrin‐Cyclophanes with 7,7,8,8‐Tetracyanoquinodimethane as an Especially Strong Electron‐Acceptor: Syntheses, Properties, Electron‐Transfer Interactions
Author(s) -
Staab Heinz A.,
Weikard Jan,
Rückemann Andreas,
Schwögler Anja
Publication year - 1998
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/(sici)1099-0690(199812)1998:12<2703::aid-ejoc2703>3.0.co;2-i
Subject(s) - porphyrin , cyclophane , tetracyanoquinodimethane , chemistry , electron acceptor , electron transfer , acceptor , photochemistry , intramolecular force , photoinduced electron transfer , electron donor , crystallography , crystal structure , stereochemistry , organic chemistry , molecule , catalysis , physics , condensed matter physics
Previous work on intramolecular electron‐transfer compounds of the quinone‐porphyrin cyclophane type with gradually increasing electron‐acceptor strength was now extended to acceptor‐porphyrin cyclophanes with 7,7,8,8‐tetracyanoquinodimethane (TCNQ) as an especially strong electron‐acceptor. The vertically stacked TCNQ‐porphyrin cyclophane 1 was prepared in a multi‐step synthesis. Physical properties related to structure and electron‐transfer processes of 1 are reported. To determine the distance dependence of the interaction between the electron‐acceptor TCNQ and the porphyrin, first results on the synthesis of the corresponding naphthalene‐spacered TCNQ‐porphyrin cyclophane 15 are presented.