A method for controlling the synthesis of stable twisted two-dimensional conjugated molecules

Yongjun Li (), Zhiyu Jia, Shengqiang Xiao, Huibiao Liu and Yuliang Li ()
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Yongjun Li: CAS Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
Zhiyu Jia: CAS Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
Shengqiang Xiao: State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology
Huibiao Liu: CAS Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences
Yuliang Li: CAS Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science (BNLMS), Institute of Chemistry, Chinese Academy of Sciences

Nature Communications, 2016, vol. 7, issue 1, 1-11

Abstract: Abstract Thermodynamic stabilization (π-electron delocalization through effective conjugation) and kinetic stabilization (blocking the most-reactive sites) are important considerations when designing stable polycyclic aromatic hydrocarbons displaying tunable optoelectronic properties. Here, we demonstrate an efficient method for preparing a series of stable two-dimensional (2D) twisted dibenzoterrylene-acenes. We investigated their electronic structures and geometries in the ground state through various experiments assisted by calculations using density functional theory. We find that the length of the acene has a clear effect on the photophysical, electrochemical, and magnetic properties. These molecules exhibit tunable ground-state structures, in which a stable open-shell quintet tetraradical can be transferred to triplet diradicals. Such compounds are promising candidates for use in nonlinear optics, field effect transistors and organic spintronics; furthermore, they may enable broader applications of 2D small organic molecules in high-performance electronic and optical devices.

Date: 2016
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DOI: 10.1038/ncomms11637

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