Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 19, Pages 7504-7513Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo901769c
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Funding
- National Science Foundation [CHE-0718117]
- National Science Foundation/Department of Energy [CHE-0087817]
- U.S. Department of Energy, Basic Energy Sciences, Office of Science [W-31-109Eng-38]
- Grants-in-Aid for Scientific Research [21350025] Funding Source: KAKEN
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0718117] Funding Source: National Science Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0822838] Funding Source: National Science Foundation
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The functionalized, enantiomerically pure [7]helicene 1 derived from bis(benzodithiophene) functionalized with four heptyl groups is prepared from 1,8-dibromo-4,5-diheptylbenzo[1,2-b:4,3-b']dithiophene building block 2. Such [7]helicene structure, functionalized with bromines at the terminal positions of the helicene inner rim and multiple solubilizing alkyl groups, is an attractive building block for long [n]helicenes and oligo[7]helicenes. Chirooptical properties and the degree of electron delocalization are determined and compared to those of analogous carbon-sulfur [7]helicene and [7]helicenes derived from benzodithiophene to provide a correlation between chirooptical properties and the degree of electron delocalization. [7]Helicene 1 possesses a moderately increased electron delocalization, but its chirooptical properties are similar to those for analogous [7]helicenes with relatively lower electron delocalization, indicating that chirooptical properties are not significantly affected by electron delocalization for this series of [7]helicenes. Molecular structures of racemic [7]helicene 1 and its benzodithiophene building block 2 are confirmed by single-crystal X-ray analysis. Crystals of 2 are chiral and adopt the shape of long, flexible, flat needles that can be readily bent.
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