148080-35-7Relevant academic research and scientific papers
The design of nonlinear optical chromophores exhibiting large electro-optic activity and high thermal stability: The role of donor groups
Liu, Fenggang,Xiao, Hongyan,Yang, Yuhui,Wang, Haoran,Zhang, Hua,Liu, Jialei,Bo, Shuhui,Zhen, Zhen,Liu, Xinhou,Qiu, Ling
, p. 138 - 147 (2016/03/30)
A novel chromophore based on N-(4-dibutylaminophenyl)tetrahydroquinolinyl donor group was synthesized to compare with traditional chromophores based on either diethylaminophenyl or triarylaminophenyl donor groups. Cyclic voltammetry measurements showed th
Thiophene-based dyes for probing membranes
López-Duarte, Ismael,Chairatana, Phoom,Wu, Yilei,Pérez-Moreno, Javier,Bennett, Philip M.,Reeve, James E.,Boczarow, Igor,Kaluza, Wojciech,Hosny, Neveen A.,Stranks, Samuel D.,Nicholas, Robin J.,Clays, Koen,Kuimova, Marina K.,Anderson, Harry L.
, p. 3792 - 3802 (2015/03/30)
We report the synthesis of four new cationic dipolar push-pull dyes, together with an evaluation of their photophysical and photobiological characteristics pertinent to imaging membranes by fluorescence and second harmonic generation (SHG). All four dyes consist of an N,N-diethylaniline electron-donor conjugated to a pyridinium electron-acceptor via a thiophene bridge, with either vinylene (-CHCH-) or ethynylene (-CC-) linking groups, and with either singly-charged or doubly-charged pyridinium terminals. The absorption and fluorescence behavior of these dyes were compared to a commercially available fluorescent membrane stain, the styryl dye FM4-64. The hyperpolarizabilities of all dyes were compared using hyper-Rayleigh scattering at 800 nm. Cellular uptake, localization, toxicity and phototoxicity were evaluated using tissue cell cultures (HeLa, SK-OV-3 and MDA-231). Replacing the central alkene bridge of FM4-64 with a thiophene does not substantially change the absorption, fluorescence or hyperpolarizability, whereas changing the vinylene-links to ethynylenes shifts the absorption and fluorescence to shorter wavelengths, and reduces the hyperpolarizability by about a factor of two. SHG and fluorescence imaging experiments in live cells showed that the doubly-charged thiophene dyes localize in plasma membranes, and exhibit lower internalization rates compared to FM4-64, resulting in less signal from the cell cytosol. At a typical imaging concentration of 1 μM, the doubly-charged dyes showed no significant light or dark toxicity, whereas the singly-charged dyes are phototoxic even at 0.5 μM. The doubly-charged dyes showed phototoxicity at concentrations greater than 10 μM, although they do not generate singlet oxygen, indicating that the phototoxicity is type I rather than type II. The doubly-charged thiophene dyes are more effective than FM4-64 as SHG dyes for live cells.
Novel organic dyes for efficient dye-sensitized solar cells
Li, Shao-Lu,Jiang, Ke-Jian,Shao, Ke-Feng,Yang, Lian-Ming
, p. 2792 - 2794 (2008/09/19)
Two novel metal-free organic dyes containing thienothiophene and thiophene segments have been synthesized. Nano-crystalline TiO2 dye-sensitized solar cells were fabricated using these dyes as light-harvesting sensitizers, and a high solar energ
Novel Push-Pull Thiophenes for Second Order Nonlinear Optical Applications
Rao, V. Pushkara,Jen, Alex K-Y.,Wong, K. Y.,Drost, Kevin J.
, p. 1747 - 1750 (2007/10/02)
Second order molecular nonlinear optical properties of push-pull stilbenes can be substantially increased by replacing benzene rings with thiophene rings.Synthesis and molecular nonlinear optical properties of several dialkylamino-nitro substituted thioph
Functionalized Thiophenes: Second-order Nonlinear Optical Materials
Jen, Alex K-Y.,Rao, V. Pushkara,Wong, K. Y.,Drost, Kevin J.
, p. 90 - 92 (2007/10/02)
It is shown experimentally that the complete replacement of benzene rings with thiophene rings in a donor-acceptor substituted stilbene significantly enhances its second-order nonlinear optical hyperpolarizability (β); results obtained with a series of th
