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

doi:10.1039/C5SC00304K

Title: A divergent route to core- and peripherally functionalized diazacoronenes that act as colorimetric and fluorescence proton sensors

Journal Article · Tue Mar 31 00:00:00 EDT 2015 · Chemical Science

DOI:https://doi.org/10.1039/C5SC00304K· OSTI ID:1214427

He, Bo ^[1]; Dai, Jing ^[2]; Zherebetskyy, Danylo ^[1]; Chen, Teresa L. ^[1]; Zhang, Benjamin A. ^[1]; Teat, Simon J. ^[1]; Zhang, Qichun ^[3]; Wang, Linwang ^[1]; Liu, Yi ^[1]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Zhejiang Univ., Hangzhou (China)
Nanying Technological Univ. (Singapore)

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. Furthermore, these azacoronene derivatives display significant acid-induced spectroscopic changes, suggesting their great potential as colorimetric and fluorescence proton sensors.

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Research Organization:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Advanced Research Projects Agency - Energy (ARPA-E); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1214427

Journal Information:: Chemical Science, Vol. 6, Issue 5; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 59 works

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