The Effect of Branching on the One- and Two-Photon Absorption, Cell Viability, and Localization of Cationic Triarylborane Chromophores with Dipolar versus Octupolar Charge Distributions for Cellular Imaging

被引:50
作者
Griesbeck, Stefanie [1 ,2 ]
Michail, Evripidis [3 ]
Rauch, Florian [1 ,2 ]
Ogasawara, Hiroaki [4 ]
Wang, Chenguang [4 ]
Sato, Yoshikatsu [4 ]
Edkins, Robert M. [1 ,2 ,5 ]
Zhang, Zuolun [1 ,2 ,6 ]
Taki, Masayasu [4 ]
Lambert, Christoph [3 ]
Yamaguchi, Shigehiro [4 ]
Marder, Todd B. [1 ,2 ]
机构
[1] Julius Maximilians Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany
[2] Julius Maximilians Univ Wurzburg, Inst Sustainable Chem & Catalysis Boron, D-97074 Wurzburg, Germany
[3] Julius Maximilians Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[4] Nagoya Univ, Inst Transformat Biomol, Nagoya, Aichi, Japan
[5] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow, Lanark, Scotland
[6] Jilin Univ, Coll Chem, State Key Lab Supramol Struct & Mat, Qianjin St, Changchun, Jilin, Peoples R China
关键词
boranes; cell imaging; fluorescence; lysosome; two-photon excited fluorescence; NONLINEAR-OPTICAL-PROPERTIES; A-PI-A; MOLECULAR-STRUCTURES; FLUORESCENT-PROBE; TRIVALENT BORON; SINGLE-PHOTON; PHOTOPHYSICAL PROPERTIES; COOPERATIVE ENHANCEMENT; FLUOROPHORES SYNTHESIS; ORGANOBORON COMPOUNDS;
D O I
10.1002/chem.201902461
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and nonlinear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.
引用
收藏
页码:13164 / 13175
页数:12
相关论文
共 88 条
[21]   ENERGY GAP LAW FOR RADIATIONLESS TRANSITIONS IN LARGE MOLECULES [J].
ENGLMAN, R ;
JORTNER, J .
MOLECULAR PHYSICS, 1970, 18 (02) :145-+
[22]  
Entwistle C.D., 2002, Angew. Chem, V114, P3051
[23]   Applications of three-coordinate organoboron compounds and polymers in optoelectronics [J].
Entwistle, CD ;
Marder, TB .
CHEMISTRY OF MATERIALS, 2004, 16 (23) :4574-4585
[24]  
Entwistle CD, 2002, ANGEW CHEM INT EDIT, V41, P2927, DOI 10.1002/1521-3773(20020816)41:16<2927::AID-ANIE2927>3.0.CO
[25]  
2-L
[26]   Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A-π-A systems containing E-dimesitylborylethenyl acceptors [J].
Entwistle, Christopher D. ;
Collings, Jonathan C. ;
Steffen, Andreas ;
Palsson, Lars-Olof ;
Beeby, Andrew ;
Albesa-Jove, David ;
Burke, Jacquelyn M. ;
Batsanov, Andrei S. ;
Howard, Judith A. K. ;
Mosely, Jackie A. ;
Poon, Suk-Yue ;
Wong, Wai-Yeung ;
Ibersiene, Fatima ;
Fathallah, Sofiane ;
Boucekkine, Abdou ;
Halet, Jean-Francois ;
Marder, Todd B. .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (40) :7532-7544
[27]  
Fanshun M., 2004, CHEM LETT, V33, P470
[28]   Triphenylamine isophorone derivatives with two photon absorption: Photo-physical property, DFT study and bio-imaging [J].
Gan, Xiaoping ;
Wang, Yang ;
Ge, Xinping ;
Li, Wei ;
Zhang, Xiuzhen ;
Zhu, Weiju ;
Zhou, Hongping ;
Wu, Jieying ;
Tian, Yupeng .
DYES AND PIGMENTS, 2015, 120 :65-73
[29]   Optimization of Aqueous Stability versus π-Conjugation in Tetracationic Bis(triarylborane) Chromophores: Applications in Live-Cell Fluorescence Imaging [J].
Griesbeck, Stefanie ;
Ferger, Matthias ;
Czernetzi, Corinna ;
Wang, Chenguang ;
Bertermann, Ruediger ;
Friedrich, Alexandra ;
Haehnel, Martin ;
Sieh, Daniel ;
Taki, Masayasu ;
Yamaguchi, Shigehiro ;
Marder, Todd B. .
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (32) :7679-7688
[30]   Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells [J].
Griesbeck, Stefanie ;
Michail, Evripidis ;
Wang, Chenguang ;
Ogasawara, Hiroaki ;
Lorenzen, Sabine ;
Gerstner, Lukas ;
Zang, Theresa ;
Nitsch, Joern ;
Sato, Yoshikatsu ;
Bertermann, Ruediger ;
Taki, Masayasu ;
Lambert, Christoph ;
Yamaguchi, Shigehiro ;
Marder, Todd B. .
CHEMICAL SCIENCE, 2019, 10 (20) :5405-5422