Synthesis, crystals of centrosymmetric triphenylamine chromophores bearing prodigious two-photon absorption cross-section and biological imaging.
Two centrosymmetric D-π-D type triphenylamine chromophores with long π-conjugated bridge and strong electron-donating moiety were designed, synthesized and fully characterized. The crystal analysis revealed that multiple CH⋯π interactions existed in two chromophores, which played a crucial role in generating molecular 1D chains and 2D layers structures. Linear and nonlinear optical properties of the chromophores were systematically investigated with the aid of theoretical calculations. Two chromophores both exhibited intense and wide-dispersed one-photon/two-photon excited fluorescence, bear prodigious 2PA cross section (δ). Especially for Dye2, with ethyoxyl groups, displayed the strong 2PA activity, large cross-sections (δmax>16,000GM) and high NLO efficiency (δmax/MW>16GM/(g·mol)) in the range of 680-830nm in DMF. In addition, one- and two-photon fluorescence microscopy images of HepG2 cells incubated with Dye2 were obtained and found that Dye2 could effectively uptake toward living cells and display a uniformly localized in cytosolic space.
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Shichao
S
Wang
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Shasha
S
Xu
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Yiming
Y
Wang
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Xiaohe
X
Tian
Department of Physics and Electronics, Shandong Normal University, Jinan 250014, PR China.
Yujin
Y
Zhang
Department of Physics and Electronics, Shandong Normal University, Jinan 250014, PR China.
Chuankui
C
Wang
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Jieying
J
Wu
Department of Chemistry, Anhui University, Hefei 230601, PR China.
Jiaxiang
J
Yang
Department of Chemistry, Anhui University, Hefei 230601, PR China; State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, PR China. Electronic address: yptian@ahu.edu.cn.
Yupeng
Y
Tian
D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D056945:Hep G2 Cells; D006801:Humans; D036641:Microscopy, Fluorescence, Multiphoton / Q000379:methods*
D005456:Fluorescent Dyes
Biological image; Crystal structures; Triphenylamine; Two-photon absorption