Pyrene-based color-tunable dipolar molecules: Synthesis, characterization and optical properties
journal contributionposted on 2018-04-23, 08:19 authored by Chuan-Zeng Wang, Xing Feng, Zannatul Kowser, Chong Wu, Thamina Akther, Mark ElsegoodMark Elsegood, Carl Redshaw, Takehiko Yamato
© 2018 Elsevier Ltd A controllable regioselective approach to achieve dipolar functionalization at the active sites (1,3-positions) and K-region (5,9-positions) of pyrene is demonstrated. Following this strategy, a set of dipolar 1,3-diphenyl-5,9-di(4-R-phenylethynyl)pyrenes were synthesized and systematically investigated by 1 H/ 13 C NMR spectroscopy, X-ray crystallography, electronic spectra, as well as by theoretical calculations. By adjusting the substituents at the 5,9-positions of pyrene, the pyrene-based dipolar molecules 4 (H, F, OMe, CN, CHO, NMe 2 ) exhibit tunable optical properties with a wide emission band from blue (437 nm) to orange-red (571 nm).
This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)”. We would like to thank the National Science Foundation of China (No. 21602014), Fund Program for the Scientific Activities of Selected Returned Overseas Professionals of Beijing, the OTEC at Saga University and the International Cooperation Projects of Guizhou Province (No. 20137002), the Royal Society of Chemistry for financial support, and the EPSRC for an overseas travel grant to C.R.