Jump to main content
Jump to site search

Issue 87, 2017, Issue in Progress
Previous Article Next Article

Carbazole-based compounds containing aldehyde and cyanoacetic acid: optical properties and applications in photopolymerization

Author affiliations

Abstract

Carbazole-based dyes containing aldehyde and cyanoacetic acid groups were synthesized through Sonogashira coupling and Knoevenagel reactions. These compounds included 6-((4-(diphenylamino)phenyl)ethynyl)-9-ethyl-9H-carbazole-3-carbaldehyde (CCC), 9-ethyl-6-((9-ethyl-9H-carbazol-3-yl)ethynyl)-9H-carbazole-3-carbaldehyde (TCC), (E)-2-cyano-3-(9-ethyl-6-((9-ethyl-9H-carbazol-3-yl)ethynyl)-9H-carbazol-3-yl)acrylic acid (CCN) and (E)-2-cyano-3-(6-((4-(diphenylamino)phenyl)ethynyl)-9-ethyl-9H-carbazol-3-yl)acrylic acid (TCN). Density functional theory (DFT) calculations revealed these structures to be coplanar-conjugated molecular and uniform in shape. The UV spectra showed three main absorption peaks from 240 nm to 400 nm, indicating π–π* and n–π* electron transitions. The calculated vertical singlet excitation energy was within the range of n–π*. This finding was confirmed based on the acceptor results in reduced highest occupied molecular orbital-lowest unoccupied molecular orbital gap by launching cyanoacetic acid. These functional compounds could be used as dyes/photosensitizers.

Graphical abstract: Carbazole-based compounds containing aldehyde and cyanoacetic acid: optical properties and applications in photopolymerization

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Oct 2017, accepted on 23 Nov 2017 and first published on 05 Dec 2017


Article type: Paper
DOI: 10.1039/C7RA11887B
RSC Adv., 2017,7, 55382-55388
  • Open access: Creative Commons BY license
  •   Request permissions

    Carbazole-based compounds containing aldehyde and cyanoacetic acid: optical properties and applications in photopolymerization

    H. A. Abro, T. Zhou, W. Han, T. Xue and T. Wang, RSC Adv., 2017, 7, 55382
    DOI: 10.1039/C7RA11887B

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements