Intramolecular light-induced electron transfer in a rigid, fixed-distance anthracene-N,N-dimethylaniline system. Exciplex-like behavior

• Published in: Journal of the American Chemical Society Vol. 112; no. 7; pp. 2823 - 2824
• Main Authors: Wasielewski, Michael R, Minsek, David W, Niemczyk, Mark P, Svec, Walter A, Yang, Nien Chu C
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.03.1990
• Subjects: 400500 - Photochemistry; AMINES; ANILINE; ANTHRACENE; AROMATICS; CHEMISTRY; CONDENSED AROMATICS; DATA; DATA ANALYSIS; ELECTRON TRANSFER; EMISSION SPECTROSCOPY; Exact sciences and technology; EXPERIMENTAL DATA; FLUORESCENCE SPECTROSCOPY; General and physical chemistry; HYDROCARBONS; INFORMATION; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; MEASURING METHODS; NUMERICAL DATA; ORGANIC COMPOUNDS; PHOTOCHEMISTRY; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); SPECTROSCOPY; Exciplex; Intramolecular reaction; Fluorescence spectrum; Tertiary amine; Electron transfer; Polycyclic compound; Aromatic compound; Quantum yield
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00163a066

In connection with the authors interest in light-induced electron transfer in rigid molecules, 2-(N,N-dimethylamino)-5,14-ethanopentacene (1) was synthesized. The anthracene electron acceptor and (N,N-dimethylamino)phenyl electron donor in 1 are held rigidly in a spatial configuration such that they are prevented from undergoing large structural changes before or after excitation. The fluorescence spectroscopy of 1 was investigated in solvents of differing polarity in order to probe for electron transfer from the (N,N-dimethylamino)phenyl donor to the excited anthracene acceptor, and the results are given.