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Molecules 2018, 23(2), 421; https://doi.org/10.3390/molecules23020421

Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study

1
Department of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New Zealand
2
ARC Centre of Excellence for Electromaterials Science, University of Wollongong, Wollongong, NSW 2522, Australia
3
Intelligent Polymer Research Institute/AIIM Faculty, Innovation Campus, University of Wollongong, Wollongong, NSW 2522, Australia
*
Authors to whom correspondence should be addressed.
Received: 7 January 2018 / Revised: 8 February 2018 / Accepted: 12 February 2018 / Published: 14 February 2018
(This article belongs to the Special Issue Advanced Functional Dyes)
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Abstract

A series of eight carbazole-cyanoacrylate based donor-acceptor dyes were studied. Within the series the influence of modifying the thiophene bridge, linking donor and acceptor and a change in the nature of the acceptor, from acid to ester, was explored. In this joint experimental and computational study we have used electronic absorbance and emission spectroscopies, Raman spectroscopy and computational modeling (density functional theory). From these studies it was found that extending the bridge length allowed the lowest energy transition to be systematically red shifted by 0.12 eV, allowing for limited tuning of the absorption of dyes using this structural motif. Using the aforementioned techniques we demonstrate that this transition is charge transfer in nature. Furthermore, the extent of charge transfer between donor and acceptor decreases with increasing bridge length and the bridge plays a smaller role in electronically mixing with the acceptor as it is extended. View Full-Text
Keywords: donor-acceptor dyes; carbazole; cyanoacrylate; thiophene; resonance Raman; TD-DFT; charge transfer donor-acceptor dyes; carbazole; cyanoacrylate; thiophene; resonance Raman; TD-DFT; charge transfer
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Sutton, J.J.; Barnsley, J.E.; Mapley, J.I.; Wagner, P.; Officer, D.L.; Gordon, K.C. Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study. Molecules 2018, 23, 421.

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