Electron-Transporting Bis(heterotetracenes) with Tunable Helical Packing

Zeng C, Xiao C, Feng X, Zhang L, Jiang W, Wang Z (2018)

Publication Type: Journal article

Publication year: 2018

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 57

Pages Range: 10933-10937

Journal Issue: 34

DOI: 10.1002/anie.201805614

Abstract

A novel kind of electron-deficient bis(heterotetracenes) namely perylenotetrathiophenediimides (PTTIs) involving double S-hetero[5]helicene diimides, is developed by a fourfold thienannulation route via ortho-functionalization of perylene diimides (PDIs). PTTIs exhibit significantly red-shifted absorption capacity with lowest-energy transition maxima beyond 700 nm and narrowed HOMO–LUMO energy gaps. Through delicately tuning the side-chain substitution, the distorted propeller-like framework could self-assemble into unprecedented 1D helical π-stacking structures with short π–π contacts and rich nonbonding interactions from alternating arrangements of P/M enantiomeric couples or tetrads. Excellent electron transporting efficiency in racemate PTTI crystals with 0.40 cm2 V−1 s−1 for 5 a and 0.90 cm2 V−1 s−1 for 5 b, was witnessed in single-crystalline transistors, signifying the prospects of the chiral π-helix in optoelectronic applications.

Involved external institutions

Chinese Academy of Sciences (CAS) / 中国科学院 CN China (CN) Beijing University of Chemical Technology CN China (CN) Technische Universität Dresden DE Germany (DE)

How to cite

APA:

Zeng, C., Xiao, C., Feng, X., Zhang, L., Jiang, W., & Wang, Z. (2018). Electron-Transporting Bis(heterotetracenes) with Tunable Helical Packing. Angewandte Chemie International Edition, 57(34), 10933-10937. https://doi.org/10.1002/anie.201805614

MLA:

Zeng, Cheng, et al. "Electron-Transporting Bis(heterotetracenes) with Tunable Helical Packing." Angewandte Chemie International Edition 57.34 (2018): 10933-10937.

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