A Luminescent Nitrogen-Containing Polycyclic Aromatic Hydrocarbon Synthesized by Photocyclodehydrogenation with Unprecedented Regioselectivity
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AbstractWe present a nitrogen-containing polycyclic aromatic hydrocarbon (N-PAH), namely 12-methoxy-9-(4-methoxyphenyl)-5,8-diphenyl-4-(pyridin-4-yl) pyreno[1,10,9-h,i,j]-isoquinoline (c-TPE-ON), which exhibits high quantum-yield emission both in solution (blue) and in the solid state (yellow). This molecule was unexpectedly obtained by a three-fold, highly regioselective photocyclodehydrogenation of a tetraphenylethylene-derived AIEgen. Based on manifold approaches involving UV/Vis, photoluminescence, and NMR spectroscopy as well as HRMS, we propose a reasonable mechanism for the formation of the disk-like N-PAH that is supported by density functional theory calculations. In contrast to most PAHs that are commonly used, our system does not suffer from entire fluorescence quenching in the solid state due to the peripheral aromatic rings preventing p-p stacking interactions, as evidenced by single-crystal X-ray analysis. Moreover, its rod-like microcrystals exhibit excellent optical waveguide properties. Hence, c-TPE-ON comprises a N-PAH with unprecedented luminescent properties and as such is a promising candidate for fabricating organic optoelectronic devices. Our design and synthetic strategy might lead to a more general approach to the preparation of solution-and solid-state luminescent PAHs.
All Author(s) ListGu XG, Wang H, Roose J, He ZK, Zhou Y, Yan YL, Cai YJ, Shi HP, Zhang YL, Sung HHY, Lam JWY, Miao Q, Zhao YS, Wong KS, Williams ID, Tang BZ
Journal nameChemistry - A European Journal
Year2015
Month12
Day1
Volume Number21
Issue Number49
PublisherWILEY-V C H VERLAG GMBH
Pages17973 - 17980
ISSN0947-6539
eISSN1521-3765
LanguagesEnglish-United Kingdom
Keywordsaggregation; luminescence; optical waveguides; polycycles; regioselectivity
Web of Science Subject CategoriesChemistry; Chemistry, Multidisciplinary

Last updated on 2020-24-10 at 02:46