Synthesis and photochemical study of substituted heterohelicenes and related compounds

Ying Hu; Brigitte Wex; Marc W. Perkovic; Douglas C. Neckers

doi:10.1117/12.698698

14 September 2006 Synthesis and photochemical study of substituted heterohelicenes and related compounds

Ying Hu, Brigitte Wex, Marc W. Perkovic, Douglas C. Neckers

Proceedings Volume 6331, Linear and Nonlinear Optics of Organic Materials VI; 63311A (2006) https://doi.org/10.1117/12.698698
Event: SPIE Optics + Photonics, 2006, San Diego, California, United States

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.

Citation Download Citation

Ying Hu, Brigitte Wex, Marc W. Perkovic, and Douglas C. Neckers "Synthesis and photochemical study of substituted heterohelicenes and related compounds", Proc. SPIE 6331, Linear and Nonlinear Optics of Organic Materials VI, 63311A (14 September 2006); https://doi.org/10.1117/12.698698

ACCESS THE FULL ARTICLE

INSTITUTIONAL
Select your institution to access the SPIE Digital Library.

SELECT YOUR INSTITUTION

PERSONAL
Sign in with your SPIE account to access your personal subscriptions or to use specific features such as save to my library, sign up for alerts, save searches, etc.

PERSONAL SIGN IN

No SPIE Account? Create one

PURCHASE THIS CONTENT

SUBSCRIBE TO DIGITAL LIBRARY

50 downloads per 1-year subscription

Members: $195

Non-members: $335 ADD TO CART

25 downloads per 1 - year subscription

Members: $145

Non-members: $250 ADD TO CART

PURCHASE SINGLE ARTICLE

Includes PDF, HTML & Video, when available