A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors
Combining core annulation and peripheral group modification, we have demonstrated a divergent synthesis of a family of highly functionalized coronene derivatives from a readily accessible dichlorodiazaperylene intermediate. Various reactions, such as aromatic nucleophilic substitution, Kumada coupli...
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sg-ntu-dr.10356-961942023-07-14T15:57:18Z A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors He, Bo Dai, Jing Zherebetskyy, Danylo Chen, Teresa L. Zhang, Benjamin A. Teat, Simon J. Zhang, Qichun Wang, Linwang Liu, Yi School of Materials Science & Engineering DRNTU::Engineering::Materials::Functional materials Combining core annulation and peripheral group modification, we have demonstrated a divergent synthesis of a family of highly functionalized coronene derivatives from a readily accessible dichlorodiazaperylene intermediate. Various reactions, such as aromatic nucleophilic substitution, Kumada coupling and Suzuki coupling proceed effectively on α-positions of the pyridine sites, giving rise to alkoxy, thioalkyl, alkyl or aryl substituted polycyclic aromatic hydrocarbons. In addition to peripheral group modulation, the aromatic core structures can be altered by annulation with thiophene or benzene ring systems. Corresponding single crystal X-ray diffraction and optical studies indicate that the heteroatom linkages not only impact the solid state packing, but also significantly influence the optoelectronic properties. Moreover, these azacoronene derivatives display significant acid-induced spectroscopic changes, suggesting their great potential as colorimetric and fluorescence proton sensors. Published version 2015-08-20T08:28:53Z 2019-12-06T19:26:52Z 2015-08-20T08:28:53Z 2019-12-06T19:26:52Z 2015 2015 Journal Article He, B., Dai, J., Zherebetskyy, D., Chen, T. L., Zhang, B. A., Teat, S. J., Zhang, Q., Wang, L.,& Liu, Y. (2015). A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors. Chem. Sci., 6(5), 3180-3186. He, B., Dai, J., Zherebetskyy, D., Chen, T. L., Zhang, B. A., Teat, S. J., Zhang, Q., Wang, L., & Liu, Y. (2015). A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors. Chem. Sci., 6(5), 3180-3186. 2041-6520 https://hdl.handle.net/10356/96194 http://hdl.handle.net/10220/38478 10.1039/C5SC00304K en Chemical science © 2015 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. 7 p. application/pdf |
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DRNTU::Engineering::Materials::Functional materials He, Bo Dai, Jing Zherebetskyy, Danylo Chen, Teresa L. Zhang, Benjamin A. Teat, Simon J. Zhang, Qichun Wang, Linwang Liu, Yi A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
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Combining core annulation and peripheral group modification, we have demonstrated a divergent synthesis of a family of highly functionalized coronene derivatives from a readily accessible dichlorodiazaperylene intermediate. Various reactions, such as aromatic nucleophilic substitution, Kumada coupling and Suzuki coupling proceed effectively on α-positions of the pyridine sites, giving rise to alkoxy, thioalkyl, alkyl or aryl substituted polycyclic aromatic hydrocarbons. In addition to peripheral group modulation, the aromatic core structures can be altered by annulation with thiophene or benzene ring systems. Corresponding single crystal X-ray diffraction and optical studies indicate that the heteroatom linkages not only impact the solid state packing, but also significantly influence the optoelectronic properties. Moreover, these azacoronene derivatives display significant acid-induced spectroscopic changes, suggesting their great potential as colorimetric and fluorescence proton sensors. |
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School of Materials Science & Engineering |
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School of Materials Science & Engineering He, Bo Dai, Jing Zherebetskyy, Danylo Chen, Teresa L. Zhang, Benjamin A. Teat, Simon J. Zhang, Qichun Wang, Linwang Liu, Yi |
format |
Article |
author |
He, Bo Dai, Jing Zherebetskyy, Danylo Chen, Teresa L. Zhang, Benjamin A. Teat, Simon J. Zhang, Qichun Wang, Linwang Liu, Yi |
author_sort |
He, Bo |
title |
A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
title_short |
A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
title_full |
A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
title_fullStr |
A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
title_full_unstemmed |
A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
title_sort |
divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors |
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2015 |
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https://hdl.handle.net/10356/96194 http://hdl.handle.net/10220/38478 |
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1773551273094676480 |