Journal
ORGANIC LETTERS
Volume 14, Issue 12, Pages 3076-3079Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol3011437
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- National Science Foundation [CHE-0718117, CHE-1012578]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1012578] Funding Source: National Science Foundation
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Asymmetric synthesis of (-)-[9]helicene, as well as preparation of its lower homologues, completes the series of carbon-sulfur [5]-, [7]-, [9]-, and [11]helicenes. Spectroscopic and electrochemical studies of this series provide an absorption onset-based band gap, E-g = 3.40 eV, for a cross-conjugated (C2S)(n) helix; this value may be compared to E-g = 3.59 eV obtained from TD-DFT computed excitation energies for a series of dimethyl-substituted [n]helicenes (n <= 31).
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