Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study
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 s...
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MDPI AG
2018-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/2/421 |
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| author | Joshua J. Sutton Jonathan E. Barnsley Joseph I. Mapley Pawel Wagner David L. Officer Keith C. Gordon |
| author_facet | Joshua J. Sutton Jonathan E. Barnsley Joseph I. Mapley Pawel Wagner David L. Officer Keith C. Gordon |
| author_sort | Joshua J. Sutton |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-13T07:40:24Z |
| format | Article |
| id | doaj.art-0e5be7b258a04495a32726fbb67f9912 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-13T07:40:24Z |
| publishDate | 2018-02-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-0e5be7b258a04495a32726fbb67f99122022-12-21T23:54:58ZengMDPI AGMolecules1420-30492018-02-0123242110.3390/molecules23020421molecules23020421Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational StudyJoshua J. Sutton0Jonathan E. Barnsley1Joseph I. Mapley2Pawel Wagner3David L. Officer4Keith C. Gordon5Department of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New ZealandDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New ZealandDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New ZealandARC Centre of Excellence for Electromaterials Science, University of Wollongong, Wollongong, NSW 2522, AustraliaARC Centre of Excellence for Electromaterials Science, University of Wollongong, Wollongong, NSW 2522, AustraliaDepartment of Chemistry, University of Otago, P.O. Box 56, Dunedin 9054, New ZealandA 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.http://www.mdpi.com/1420-3049/23/2/421donor-acceptor dyescarbazolecyanoacrylatethiopheneresonance RamanTD-DFTcharge transfer |
| spellingShingle | Joshua J. Sutton Jonathan E. Barnsley Joseph I. Mapley Pawel Wagner David L. Officer Keith C. Gordon Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study Molecules donor-acceptor dyes carbazole cyanoacrylate thiophene resonance Raman TD-DFT charge transfer |
| title | Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study |
| title_full | Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study |
| title_fullStr | Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study |
| title_full_unstemmed | Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study |
| title_short | Modulation of Donor-Acceptor Distance in a Series of Carbazole Push-Pull Dyes; A Spectroscopic and Computational Study |
| title_sort | modulation of donor acceptor distance in a series of carbazole push pull dyes a spectroscopic and computational study |
| topic | donor-acceptor dyes carbazole cyanoacrylate thiophene resonance Raman TD-DFT charge transfer |
| url | http://www.mdpi.com/1420-3049/23/2/421 |
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