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Title: Concise synthesis and two-photon-excited deep-blue emission of 1,8-diazapyrenes
Authors: He, Tingchao
Too, Pei Chui
Chen, Rui
Chiba, Shunsuke
Sun, Handong
Issue Date: 2012
Source: He, T., Too, P. C., Chen, R., Chiba, S.,& Sun, H. (2012). Concise Synthesis and Two-Photon-Excited Deep-Blue Emission of 1,8-Diazapyrenes. Chemistry - An Asian Journal, 7(9), 2090-2095.
Series/Report no.: Chemistry - an Asian journal
Abstract: Efficient violet–blue-emitting molecules are especially useful for applications in full-color displays, solid-state lighting, as well as in two-photon absorption (TPA) excited frequency-upconverted violet–blue lasing. However, the reported violet–blue-emitting molecules generally possess small TPA cross sections. In this work, new 1,8-diazapyrenes derivatives 3 with blue two-photon-excited fluorescence emission were concisely synthesized by the coupling reaction of readily available 1,4-naphthoquinone O,O-diacetyl dioxime (1) with internal alkynes 2 under the [{RhCl2Cp*}2]–Cu(OAc)2 (Cp*=pentamethylcyclopentadienyl ligand) bimetallic catalytic system. Elongation of the π-conjugated length of 1,8-diazapyrenes 3 led to the increase of TPA cross sections without the expense of a redshift of the emission wavelength, probably due to the rigid planar structure of chromophores. It is especially noteworthy that 2,3,6,7-tetra(4-bromophenyl)-1,8-diazapyrene (3c) has a larger TPA cross section than those of other molecules reported so far. These experimental results are explained in terms of the effects of extension of the π-conjugated system, intramolecular charge transfer, and reduced detuning energy.
ISSN: 18614728
DOI: 10.1002/asia.201200192
Fulltext Permission: none
Fulltext Availability: No Fulltext
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