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Phenothiazine−Bipyridinium Cyclophanes
Author(s) -
Bauer Helmut,
Stier Falk,
Petry Christoph,
Knorr Andreas,
Stadler Christian,
Staab Heinz A.
Publication year - 2001
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 - 10.1002/1099-0690(200109)2001:17<3255::aid-ejoc3255>3.0.co;2-0
Subject(s) - chemistry , phenothiazine , cyclophane , acceptor , dication , quenching (fluorescence) , photochemistry , fluorescence , electrochemistry , stereochemistry , crystallography , crystal structure , organic chemistry , ion , electrode , physics , quantum mechanics , condensed matter physics , medicine , pharmacology
Abstract The syntheses of oligooxa[8.8]‐, ‐[11.11]‐, ‐[14,14]‐, ‐[17.17]‐ and ‐[20.20]cyclophanes with phenothiazine as donor and bipyridinium dication as acceptor are described, together with preparations of the corresponding oligomethylene‐[3.3]‐ and ‐[4.4]cyclophanes. While the large [8.8]‐, [11.11]‐ and [14.14]cyclophanes in particular show well‐defined charge‐transfer (CT) absorption maxima, the smallest [3.3]cyclophane does not exhibit any CT effect. For the large cyclophanes, a preferred conformation with crossed donor and acceptor units is proposed. The fluorescence quenching and electrochemical behaviour of all phenothiazine−bipyridinium cyclophanes is discussed.