Thiophene fused indenocorannulenes: synthesis, variable emission, and exceptional chiral configurational stability
Literature Information
Publication Date
2021-06-16
DOI
10.1039/D1QO00596K
Impact Factor
5.281
Authors
Xiaoqi Tian, Suchaya Chaiworn, Jun Xu, Nicolas Vanthuyne, Kim K. Baldridge, Jay S. Siegel
View Original
Abstract
A set of thiophene fused indenocorannulenes (TFICs) was synthesized and characterized by X-ray crystallography, electrochemical, and photophysical methods. Two chiral derivatives were resolved and their absolute configurations defined by Flack analysis (12a) and by comparison of experimental VCD/ECD spectra with hybrid DFT methods (12b and 3a). The emission wavelengths of 13 compounds were compared and varied over 220 nm (emission colors from violet to red). The bowl-inversion activation barrier of 12 was determined to be 192.7 kJ mol−1, corresponding to a configurational stability of weeks at 200 °C; on par with the highest helicene and phosphine values.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
3-(Methylamino)-1-phenyl-1-propanone hydrochloride (1:1)
CAS Number:
2538-50-3
Molecular Formula:
C10H14ClNO
![4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline structure](https://static.chemtradehub.com/structs/120/120928-09-8-d3db.webp "4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline structure")
4-{2-[4-(2-Methyl-2-propanyl)phenyl]ethoxy}quinazoline
CAS Number:
120928-09-8
Molecular Formula:
C20H22N2O
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