Derivatizing Tribenzothiophene-Fused Hexa-peri-hexabenzocoronenes with Tunable Optoelectronic Properties

Yi Liu; Tomasz Marszalek; Klaus Müllen; Wojciech Pisula; Xinliang Feng

doi:10.1002/asia.201600753

Derivatizing Tribenzothiophene-Fused Hexa-peri-hexabenzocoronenes with Tunable Optoelectronic Properties

Chem Asian J. 2016 Aug 5;11(15):2107-12. doi: 10.1002/asia.201600753. Epub 2016 Jul 15.

Authors

Yi Liu¹, Tomasz Marszalek¹, Klaus Müllen¹, Wojciech Pisula^{2

3}, Xinliang Feng⁴

Affiliations

¹ Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
² Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany. pisula@mpip-mainz.mpg.de.
³ Department of Molecular Physics, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924, Lodz, Poland. pisula@mpip-mainz.mpg.de.
⁴ Center for Advancing Electronics Dresden (cfaed) and, Department of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany. xinliang.feng@tu-dresden.de.

PMID: 27348404
DOI: 10.1002/asia.201600753

Abstract

A series of trisbenzothieno[1,2:7,8:13,14]hexa-peri-hexabenzocoronenes were synthesized and characterized by a combination of NMR, 2D NMR, MALDI-TOF MS, UV/Vis absorption spectroscopy, and 2D-WAXS measurement. By structural modulation like decoration of electro-donating alkoxyl chain, and conversion from an electron-rich thiophene ring into an electron-poor thiophene-S,S-dioxide moiety, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels of the hexabenzocoronenes derivatives can be effectively tuned which is further verified by the DFT calculations and cyclic voltammetry.

Keywords: benzothiophene; helical packing; hexa-peri-hexabenzocoronenes; oxidation; thiophene-S,S-dioxide.