Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/96194
Title: A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors
Authors: He, Bo
Dai, Jing
Zherebetskyy, Danylo
Chen, Teresa L.
Zhang, Benjamin A.
Teat, Simon J.
Zhang, Qichun
Wang, Linwang
Liu, Yi
Keywords: DRNTU::Engineering::Materials::Functional materials
Issue Date: 2015
Source: 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.
Series/Report no.: Chemical science
Abstract: 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.
URI: https://hdl.handle.net/10356/96194
http://hdl.handle.net/10220/38478
ISSN: 2041-6520
DOI: 10.1039/C5SC00304K
Rights: © 2015 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:MSE Journal Articles

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