1228231-50-2Relevant academic research and scientific papers
Synthesis and Photophysical Properties of Phenyleneethynylenes Containing a Combination of Two Main Group Element Moieties of B, Si, or P on the Side Chain
Sanji, Takanobu,Fuchigami, Akemi,Tanaka, Masato
, p. 350 - 358 (2018)
X-shaped 1,4-phenyleneethynylenes containing a combination of two main group element moieties of B, Si, or P as part of the side chain have been synthesized. The halogen-lithium exchange of 2-bromo-5-dimethylphenylsilyl-1,4-bis(phenylethynyl)benzene followed by addition of fluorodimesitylborane or chlorodiphenylphosphine gave the X-shaped B/Si and Si/P, respectively. The P-containing molecule was oxidized to afford a P(=O) derivative. The B/PO moieties were introduced to the 1,4-phenyleneethynylene unit by 3 steps, i.e., the halogen-lithium exchange of 2,5-dibromo-1,4-bis(trimethylsilylethynyl)benzene followed by sequential addition of fluorodimesitylborane and chlorodiphenylphosphine oxide, desilylation, and the Sonogashira coupling with aryl iodides. Then, the reduction of the B/PO gave X-shaped B/P derivative. The absorption and fluorescence spectra of the X-shaped molecules showed the molecules have two-dimensional conjugation systems, i.e., the π-conjugation of the original π-conjugation backbone and p(B)π-π? conjugation of B, σ?-π? conjugation of Si, and n-π and σ?-π? conjugation of P, extended from the π-core. The highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy levels are significantly altered because of a lowering of the LUMO level due to p-π? conjugation for B and σ?-π? conjugation for Si and P compared with the parent phenyleneethynylene, which are also supported by density functional theory calculations.
Zwitterionic ladder bis(arylethenyl)benzenes with large two-photon absorption cross sections
Fukazawa, Aiko,Yamada, Hiroshi,Sasaki, Yutaka,Akiyama, Seiji,Yamaguchi, Shigehiro
supporting information; experimental part, p. 466 - 469 (2010/08/22)
Various phosphonium- and borate-bridged bis(arylethenyl)benzenes were synthesized. The large two-photon absorption (TPA) cross sections in these zwitterionic ladder π-electron systems revealed that the introduction of zwitterionic bridges in the coplanar π-conjugated framework is a powerful strategy for designing excellent TPA materials. 2010 Wiley-VCH Verlag GmbH&Co. KGaA.
