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

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. This journal is

Citation
Naibi Lakshminarayana, A., Chang, J., Luo, J., Zheng, B., Huang, K.-W., & Chi, C. (2015). Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction. Chemical Communications, 51(17), 3604–3607. doi:10.1039/c4cc09812a

Acknowledgements
This work was financially supported by a NUS start-up grant (R-143-000-486-133), MOE AcRF grants (R-143-000-510-112 and R-143-000-573-112) and a A*STAR JCO grant (1431AFG100). K.-W. Huang acknowledges financial support from KAUST.

Publisher
Royal Society of Chemistry (RSC)

Journal
Chemical Communications

DOI
10.1039/c4cc09812a

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