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Issue 17, 2015
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Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction

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Abstract

Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π–π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order.

Graphical abstract: Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction

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Article information


Submitted
09 Dec 2014
Accepted
12 Jan 2015
First published
12 Jan 2015

Chem. Commun., 2015,51, 3604-3607
Article type
Communication
Author version available

Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction

A. Naibi Lakshminarayana, J. Chang, J. Luo, B. Zheng, K. Huang and C. Chi, Chem. Commun., 2015, 51, 3604
DOI: 10.1039/C4CC09812A

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