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Proceedings Paper

Synthesis and photochemical study of substituted heterohelicenes and related compounds
Author(s): Ying Hu; Brigitte Wex; Marc W. Perkovic; Douglas C. Neckers
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Paper Abstract

Helicenes with aryl electron-withdrawing or/and electron-donating groups at one/both end/s are potential candidates for second order nonlinear optical applications. We have prepared such helicenes and related compounds. A single crystal X-ray structure showed the structure and architecture of 2,7-di-1-naphthylbenzo[1,2-b:4,3-b'] dithiophene to be racemic chiral helixes. Both terminal aryl rings contribute to the π-π stacking. Theoretically, there are two synthetic routes (A and B) for the synthesis of 2-(4-methoxylphenyl)trithia-[5]-heterohelicene and 2-(4-methoxylphenyl)-9-(4-cyanophenyl)trithia- [5]-heterohelicene. Although route A is more complicated, it is more efficient because substituents improve solubility. Introducing an electron-donating group increases the yields of all reactions in A.

Paper Details

Date Published: 14 September 2006
PDF: 7 pages
Proc. SPIE 6331, Linear and Nonlinear Optics of Organic Materials VI, 63311A (14 September 2006); doi: 10.1117/12.698698
Show Author Affiliations
Ying Hu, Bowling Green State Univ. (United States)
Brigitte Wex, Arizona State Univ. (United States)
Marc W. Perkovic, Western Michigan Univ. (United States)
Douglas C. Neckers, Bowling Green State Univ. (United States)

Published in SPIE Proceedings Vol. 6331:
Linear and Nonlinear Optics of Organic Materials VI
Robert A. Norwood, Editor(s)

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