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Electron Transfer Through Molecular Bridges Between Reducible Pentakis(thiophenyl)benzene Subunits
Author(s) -
Mayor Marcel,
Büschel Michael,
Fromm Katharina M.,
Lehn JeanMarie,
Daub Jörg
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010316)7:6<1266::aid-chem1266>3.0.co;2-s
Subject(s) - diacetylene , synthon , hydrazone , chemistry , electron transfer , crystallography , molecular wire , benzene , stereochemistry , molecule , photochemistry , organic chemistry , polymerization , polymer
“Dimers” 3, 4 and 7 , which consist of two reducible pentakis(thiophenyl)benzene subunits linked by different molecular structures, have been synthesised as model compounds for reducible molecular‐wire‐type synthons to represent differences in the electron‐transfer ability as a function of the bridging structure. The bridging units consist of para ‐divinylbenzene in 3 , bis‐hydrazone in 4 and diacetylene in 7 . Their ability to transfer electrons from one reducible subunit to the other was investigated by electrochemical and spectroelectrochemical methods and, in the case of 4 and 7 , the solid‐state structures support the experimental findings. The para ‐divinylbenzene bridge in 3 was found to completely isolate the reducible structures (Class I system). In contrast, the diacetylene bridge in 7 electronically connects the two reducible structures (Class III system) and, thus, demonstrates its potential application as a “molecular wire”. The bis‐hydrazone‐linked compound 4 displayed only a low level of electronic connection between the subunits and was only observed in the spectroelectrochemical investigation.