Qiu, Zijie, Asako, Sobi ORCID: 0000-0003-4525-5317, Hu, Yunbin ORCID: 0000-0001-5346-7059, Ju, Cheng-Wei ORCID: 0000-0002-2250-8548, Liu, Thomas, Rondin, Loic, Schollmeyer, Dieter, Lauret, Jean-Sebastien ORCID: 0000-0003-1309-4977, Muellen, Klaus and Narita, Akimitsu (2020). Negatively Curved Nanographene with Heptagonal and [5]Helicene Units. J. Am. Chem. Soc., 142 (35). S. 14814 - 14820. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-5126

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Abstract

Negatively curved nanographene (NG) 4, having two heptagons and a [5]helicene, was unexpectedly obtained by aryl rearrangement and stepwise cyclodehydrogenations. X-ray crystallography confirmed the saddle-shaped structures of intermediate 3 and NG 4. The favorability of rearrangement over helicene formation following radical cation or arenium cation mechanisms is supported by theoretical calculations. NG 4 demonstrates a reversible mechanochromic color change and solid-state emission, presumably benefiting from its loose crystal packing. After resolution by chiral high-perfomance liquid chromatography, the circular dichroism spectra of enantiomers 4-(P) and 4-(M) were measured and showed moderate Cotton effects at 350 nm (vertical bar Delta epsilon vertical bar = 148 M-1 cm(-1)).

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Qiu, ZijieUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Asako, SobiUNSPECIFIEDorcid.org/0000-0003-4525-5317UNSPECIFIED
Hu, YunbinUNSPECIFIEDorcid.org/0000-0001-5346-7059UNSPECIFIED
Ju, Cheng-WeiUNSPECIFIEDorcid.org/0000-0002-2250-8548UNSPECIFIED
Liu, ThomasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Rondin, LoicUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schollmeyer, DieterUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Lauret, Jean-SebastienUNSPECIFIEDorcid.org/0000-0003-1309-4977UNSPECIFIED
Muellen, KlausUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Narita, AkimitsuUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-319874
DOI: 10.1021/jacs.0c05504
Journal or Publication Title: J. Am. Chem. Soc.
Volume: 142
Number: 35
Page Range: S. 14814 - 14820
Date: 2020
Publisher: AMER CHEMICAL SOC
Place of Publication: WASHINGTON
ISSN: 1520-5126
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/31987

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