Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 9, 2008
Previous Article Next Article

Synthesis and structure–property relationships of donor/acceptor-functionalized bis(dehydrobenzo[18]annuleno)benzenes

Author affiliations

Abstract

Seven new bis(dehydrobenzo[18]annuleno)benzenes (bis[18]DBAs) 1–7 functionalized with electron-donating dibutylamino groups and/or accepting nitro groups at various positions along the peripheries of the chromophores have been prepared. The effects of varying the donor/acceptor charge transfer pathways, chromophore lengths and molecular symmetries upon the optical band gaps are studied using UV–visible spectroscopy, and structure–property correlations are identified. It is found that bis[18]DBAs possessing donor–π–donor and acceptor–π–acceptor pathways exhibit the smallest band gaps, especially when an acceptor–π–acceptor pathway is situated along the longest chromophore length in the molecule. The all-donor species 1 is also found to exhibit efficient fluorescence with dramatic solvatochromism. The results may have value to the rational design of future NLO/TPA device components.

Graphical abstract: Synthesis and structure–property relationships of donor/acceptor-functionalized bis(dehydrobenzo[18]annuleno)benzenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 Jan 2008, accepted on 22 Feb 2008 and first published on 17 Mar 2008


Article type: Paper
DOI: 10.1039/B800875B
Citation: Org. Biomol. Chem., 2008,6, 1569-1576

  •   Request permissions

    Synthesis and structure–property relationships of donor/acceptor-functionalized bis(dehydrobenzo[18]annuleno)benzenes

    E. L. Spitler and M. M. Haley, Org. Biomol. Chem., 2008, 6, 1569
    DOI: 10.1039/B800875B

Search articles by author

Spotlight

Advertisements