학술논문
Donor- and/or Acceptor-Substituted Expanded Radialenes: Theory, Synthesis, and Properties.
Document Type
Article
Author
Source
Subject
*LEWIS acidity
*LEWIS acids
*ALKENES
*HYDROCARBONS
*BROMINE compounds
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Language
ISSN
0022-3263
Abstract
The synthesis of donor- (D) and/or acceptor (A)-expanded [4]radialenes has been developed on the basis of readily available dibromoolefin (7), tetraethynylethene (10 and 20), and vinyl triflate (12) building blocks. The successful formation of D/A radialenes relies especially on (1) effective use of a series alkynyl protecting groups, (2) Sonogashira cross-coupling reactions, and (3) the development of ring closing reactions to form the desired macrocyclic products. The expanded [4]radialene products have been investigated by spectroscopic (UV-vis absorption and emission) and quantum chemical computational methods (density functional theory and time dependent DFT). The combined use of theory and experiment provides a basis to evaluate the extent of D/A interactions via the cross-conjugated radialene framework as well as an interpretation of the origin of D/A interactions at an orbital level. [ABSTRACT FROM AUTHOR]