Concise synthesis and two-photon-excited deep-blue emission of 1,8-diazapyrenes.

نویسندگان

  • Tingchao He
  • Pei Chui Too
  • Rui Chen
  • Shunsuke Chiba
  • Handong Sun
چکیده

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 [{RhCl(2)Cp*}(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.

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عنوان ژورنال:
  • Chemistry, an Asian journal

دوره 7 9  شماره 

صفحات  -

تاریخ انتشار 2012