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Bulletin of Materials Science

, 41:153 | Cite as

Effects of conjugation on the properties of alkynylcarbazole compounds: experimental and theoretical study

  • Hussain Ahmed Abro
  • Baodong Zhao
  • Weixiang Han
  • Xiaoyu Ma
  • Tao Wang
Article
  • 23 Downloads

Abstract

Four novel dyes containing alkynylcarbazole, namely, 2-((9H-carbazol-3-yl)ethynyl)-9-ethyl-9H-carbazole, 3,6-bis((9-ethyl-9H-carbazol-2-yl)ethynyl)-9H-carbazole, 3-(phenylethynyl)-9H-carbazole and 3,6-bis(phenylethynyl)-9H-carbazole, were synthesized on the basis of single and double substitutes by following the Sonogashira coupling method. The synthesized dyes were then assessed as novel photosensitizers in visible-light photopolymerization to evaluate the effects of conjugation on the properties of aromatic compounds. A comparison between UV–vis and TD/DFT electron transition spectra shows that \(\lambda _{\mathrm{max}}\) in theoretical ultraviolet spectra matched well with the experimental spectra; every conjugated alkynylcarbazole dye exhibits a wide absorption band in the range of 300–400 mm. Moreover, conjugation enhancement by switching carbazoleacetylene moieties caused a red shift in the absorption bands. The theoretical study showed that the maxima \(\lambda \) of these molecules ranged from \(\sim \)330 to 370 mm, corresponding to \(\pi {\rightarrow }\pi ^{*}\) and \({n}{\rightarrow }\pi ^{*}\) electron transitions. Fluorescence spectroscopic data show that the strongest emission peaks exhibit a red shift because of the addition of conjugated acetylene groups. A combination of alkynyl dyes and iodonium under a halogen lamp atmosphere by visible-light photopolymerization displayed a positive response to the cationic polymerization of bisphenol-A epoxy resin A and free-radical polymerization of tripropylene glycol diacrylate.

Keyword

Synthesis alkynylcarbazole DFT calculations photosensitizers photopolymerization 

Notes

Acknowledgements

We acknowledge the National Key R&D Plan (project grant code: 2017YFB0307800) for providing them financial support. Additionally, they are very thankful to the Beijing University of Chemical Technology CHEMCLOUDCOMPUTING platform for providing support for computational work.

Supplementary material

12034_2018_1672_MOESM1_ESM.docx (2 mb)
Supplementary material 1 (docx 2053 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  • Hussain Ahmed Abro
    • 1
    • 2
  • Baodong Zhao
    • 2
  • Weixiang Han
    • 2
  • Xiaoyu Ma
    • 2
  • Tao Wang
    • 1
    • 2
  1. 1.State Key Laboratory of Chemical Resource Engineering, College of ScienceBeijing University of Chemical TechnologyBeijingPeople’s Republic of China
  2. 2.Department of Organic Chemistry, College of ScienceBeijing University of Chemical TechnologyBeijingPeople’s Republic of China

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