Qiu, Zijie, Ju, Cheng-Wei ORCID: 0000-0002-2250-8548, Frederic, Lucas ORCID: 0000-0002-4700-2279, Hu, Yunbin ORCID: 0000-0001-5346-7059, Schollmeyer, Dieter, Pieters, Gregory ORCID: 0000-0002-3924-8287, Muellen, Klaus and Narita, Akimitsu (2021). Amplification of Dissymmetry Factors in pi-Extended [7]- and [9]Helicenes. J. Am. Chem. Soc., 143 (12). S. 4661 - 4668. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-5126

Full text not available from this repository.

Abstract

pi-Extended helicenes constitute an important class of polycyclic aromatic hydrocarbons with intrinsic chirality. Herein, we report the syntheses of pi-extended [7]helicene 4 and pi-extended [9]helicene 6 through regioselective cyclodehydrogenation in high yields, where a prefusion strategy plays a key role in preventing undesirable aryl rearrangements. The unique helical structures are unambiguously confirmed by X-ray crystal structure analysis. Compared to the parent pristine [7]helicene and [9]helicene, these novel pi-extended helicenes display significantly improved photophysical properties, with a quantum yield of 0.41 for 6. After optical resolution by chiral high-performance liquid chromatography, the chiroptical properties of enantiomers 4-P/M and 6-P/M are investigated, revealing that the small variation in helical length from [7] to [9] can cause an approximately 10-fold increase in the dissymmetry factors. The circularly polarized luminescence brightness of 6 reaches 12.6 M-1 cm(-1) as one of the highest among carbohelicenes.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Qiu, ZijieUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Ju, Cheng-WeiUNSPECIFIEDorcid.org/0000-0002-2250-8548UNSPECIFIED
Frederic, LucasUNSPECIFIEDorcid.org/0000-0002-4700-2279UNSPECIFIED
Hu, YunbinUNSPECIFIEDorcid.org/0000-0001-5346-7059UNSPECIFIED
Schollmeyer, DieterUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Pieters, GregoryUNSPECIFIEDorcid.org/0000-0002-3924-8287UNSPECIFIED
Muellen, KlausUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Narita, AkimitsuUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-596442
DOI: 10.1021/jacs.0c13197
Journal or Publication Title: J. Am. Chem. Soc.
Volume: 143
Number: 12
Page Range: S. 4661 - 4668
Date: 2021
Publisher: AMER CHEMICAL SOC
Place of Publication: WASHINGTON
ISSN: 1520-5126
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
CIRCULARLY-POLARIZED LUMINESCENCE; SPIN SELECTIVITY; HELICENEMultiple languages
Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/59644

Downloads

Downloads per month over past year

Altmetric

Export

Actions (login required)

View Item View Item