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

• Published in: Chemical science (Cambridge) Vol. 6; no. 5; pp. 3180 - 3186
• Main Authors: He, Bo, Dai, Jing, Zherebetskyy, Danylo, Chen, Teresa L, Zhang, Benjamin A, Teat, Simon J, Zhang, Qichun, Wang, Linwang, Liu, Yi
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 01.05.2015
• Subjects: Chemical reactions; Colorimetry; Derivatives; Fluorescence; INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Joining; Organic chemistry; Pyridines; Sensors
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c5sc00304k

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.