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- Title
Long‐range Through‐space Charge Transfer in a pH‐responsive Mixed Cyclophane of Pyridine and Teropyrene.
- Authors
Ghasemabadi, Parisa Ghods; Tabasi, Zahra A.; Salari, Parinaz; Zhao, Yuming; Bodwell, Graham J.
- Abstract
A large, strained (SE=44.2 kcal/mol) and conformationally flexible mixed cyclophane of pyridine and teropyrene was synthesized using two intramolecular Wurtz coupling reactions and an unprecedented Scholl reaction between the unreactive 2 positions of the pyrene systems in a triply bridged pyrenophane. Protonation of the pyridine unit results in a greatly enhanced preference for nesting in the cavity of the highly bent teropyrene system (θcalc=162.6°) and emergence of a charge transfer absorption band (λmax=592 nm) due to a long range (5.0–5.5 Å), through‐space intramolecular transition between the teropyrene and pyridinium units, which does not exist in the neutral cyclophane.
- Subjects
PYRIDINE; INTRAMOLECULAR proton transfer reactions; PROTON transfer reactions; CHARGE transfer; PYRENE
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 68, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202302404