A New Series of Quadrupolar Type Two-Photon Absorption Chromophores Bearing 11,12-Dibutoxydibenzo[a,c]-phenazine Bridged Amines; Their Applications in Two-Photon Fluorescence Imaging and Two-Photon Photodynamic Therapy

被引:129
作者
Velusamy, Marappan [1 ]
Shen, Jiun-Yi [1 ]
Lin, Jiann T. [1 ]
Lin, Yi-Chih [2 ]
Hsieh, Cheng-Chih [2 ]
Lai, Chin-Hung [2 ]
Lai, Chih-Wei [2 ]
Ho, Mei-Lin [2 ]
Chen, Yu-Chun [2 ]
Chou, Pi-Tai [2 ]
Hsiao, Jong-Kai [3 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan
[3] Natl Taiwan Univ, Inst Biomed Engn, Taipei 106, Taiwan
关键词
SINGLET-OXYGEN GENERATION; OPTICAL-DATA STORAGE; ABSORBING FLUORENE DERIVATIVES; CONJUGATED PORPHYRIN DIMERS; EXCITATION CROSS-SECTIONS; PHOTOSENSITIZED PRODUCTION; PI-A; 2-PHOTON-ABSORBING CHROMOPHORES; PHOTOPHYSICAL PROPERTIES; SILICA NANOPARTICLES;
D O I
10.1002/adfm.200900125
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of quadrupolar type two-photon absorption (2PA) chromophores 3-9 bearing a core arylamine-[a,c]phenazine-arylamine motif are synthesized in high yields. Palladium-catalyzed Stille coupling and C-N coupling reactions are utilized to prepare target chromophores. Detailed characterization and systematic studies of these molecules, including absorption and fluorescence emission, are conducted. These compounds are found to exhibit very large 2PA cross section values, for example, similar to 7000 GM at 800 nm for 8 in toluene. Two-photon-induced fluorescence imaging is successfully demonstrated in vitro using compound-8-encapsulated silica nanoparticles with excellent bio-compatibility. In combination with the capability of both one- and two-photon singlet-oxygen sensitizations, this nanocomposite demonstrates its promising potential in dual functionality toward two-photon fluorescence imaging and two-photon photodynamic therapy.
引用
收藏
页码:2388 / 2397
页数:10
相关论文
共 108 条
[1]   DETERMINATION OF ABSOLUTE FLUORESCENCE QUANTUM EFFICIENCY OF QUININE BISULFATE IN AQUEOUS-MEDIUM BY OPTOACOUSTIC SPECTROMETRY [J].
ADAMS, MJ ;
HIGHFIELD, JG ;
KIRKBRIGHT, GF .
ANALYTICAL CHEMISTRY, 1977, 49 (12) :1850-1852
[2]   ELECTRONIC-STRUCTURE CALCULATIONS ON WORKSTATION COMPUTERS - THE PROGRAM SYSTEM TURBOMOLE [J].
AHLRICHS, R ;
BAR, M ;
HASER, M ;
HORN, H ;
KOLMEL, C .
CHEMICAL PHYSICS LETTERS, 1989, 162 (03) :165-169
[3]   Relationship between two-photon absorption and the π-conjugation pathway in porphyrin arrays through dihedral angle control [J].
Ahn, TK ;
Kim, KS ;
Kim, DY ;
Noh, SB ;
Aratani, N ;
Ikeda, C ;
Osuka, A ;
Kim, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1700-1704
[4]   Design of organic molecules with large two-photon absorption cross sections [J].
Albota, M ;
Beljonne, D ;
Brédas, JL ;
Ehrlich, JE ;
Fu, JY ;
Heikal, AA ;
Hess, SE ;
Kogej, T ;
Levin, MD ;
Marder, SR ;
McCord-Maughon, D ;
Perry, JW ;
Röckel, H ;
Rumi, M ;
Subramaniam, C ;
Webb, WW ;
Wu, XL ;
Xu, C .
SCIENCE, 1998, 281 (5383) :1653-1656
[5]   Two-photon fluorescence excitation cross sections of biomolecular probes from 690 to 960 nm [J].
Albota, MA ;
Xu, C ;
Webb, WW .
APPLIED OPTICS, 1998, 37 (31) :7352-7356
[6]  
[Anonymous], 2017, J MOL STRUCT, DOI DOI 10.1016/J.MOLSTRUC.2017.03.014
[7]   A systematic femtosecond study on the two-photon absorbing D-π-A molecules-π-bridge nitrogen insertion and strength of the donor and acceptor groups [J].
Antonov, L ;
Kamada, K ;
Ohta, K ;
Kamounah, FS .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2003, 5 (06) :1193-1197
[8]  
Arnbjerg J, 2007, J PHYS CHEM A, V111, P5756, DOI [10.1021/jp071197l, 10.1021/jp0711971]
[9]   Two-photon photosensitized production of singlet oxygen: Optical and optoacoustic characterization of absolute two-photon absorption cross sections for standard sensitizers in different solvents [J].
Arnbjerg, Jacob ;
Johnsen, Mette ;
Frederiksen, Peter K. ;
Braslavsky, Silvia E. ;
Ogilby, Peter R. .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (23) :7375-7385
[10]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100