Issue 12, 2011

Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction

Abstract

Previously, we developed an iterative elongation methodology to synthesize acene esters, nitriles, and imides. The strategy uses the concept of bidirectional synthesis, and we can now make a series of electron deficient anthracene, tetracene, and pentacene derivatives via the bidirectional iterative elongation protocol. Central units, used to initiate the bidirectional elongation, were synthesized by employing a double anionic Fries rearrangement as the key step. The photophysical and electrochemical properties of these novel electron acceptors are investigated and interpreted based on the electron withdrawing power of the substitutions. An excited state charge transfer was proposed for one compound to account for its peculiar fluorescent behavior.

Graphical abstract: Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction

Supplementary files

Article information

Article type
Paper
Submitted
13 Aug 2010
Accepted
11 Jan 2011
First published
27 Apr 2011

Org. Biomol. Chem., 2011,9, 4507-4517

Synthesis of electron deficient acene derivatives via a bidirectional iterative elongation reaction

Y. Lin, C. Lin, C. Chen, S. Sun and B. Pal, Org. Biomol. Chem., 2011, 9, 4507 DOI: 10.1039/C0OB00575D

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