Nanographene Imides Featuring Dual-Core Sixfold [5]Helicenes

Guogang Liu; Tobias Koch; Yan Li; Nikos L Doltsinis; Zhaohui Wang

doi:10.1002/anie.201810734

Nanographene Imides Featuring Dual-Core Sixfold [5]Helicenes

Angew Chem Int Ed Engl. 2019 Jan 2;58(1):178-183. doi: 10.1002/anie.201810734. Epub 2018 Dec 4.

Authors

Guogang Liu^{1

2}, Tobias Koch³, Yan Li^{1

2}, Nikos L Doltsinis³, Zhaohui Wang^{1

4}

Affiliations

¹ Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
² School of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Institute for Solid State Theory and Center for Multiscale Theory & Computation, University of Münster, Wilhelm-Klemm-Strasse 10, 48149, Münster, Germany.
⁴ Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing, 100084, China.

PMID: 30417969
DOI: 10.1002/anie.201810734

Abstract

A novel kind of nanographene imide, namely pentaperylene decaimides (PPD) featuring dual-core sixfold [5]helicenes and ten imide groups, was efficiently obtained. Among the possible 28 stereoisomers, which include 14 pairs of enantiomers, only one pair of enantiomers was obtained selectively which could be separated by chiral HPLC. Single-crystal X-ray diffraction analyses revealed that it exhibits a D₂ -symmetric "four-bladed propeller" conformation composed of conjoined double "three-bladed propeller", which is very stable and could not convert into other conformations even when heated up to 200 °C. Meanwhile, enantiomerically pure PPD also exhibits an excellent resistance to thermally induced racemization, which makes it a promising candidate for various applications in chiral material science.

Keywords: X-ray diffraction; dual-core structures; helicenes; nanographene imides; optoelectronic properties.

Abstract

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