Two-photon absorption in a series of 2,6-disubstituted BODIPY dyes

被引：22

作者：

Barros, Leonardo W. T. ^{[1
]}

Cardoso, Thiago A. S. ^{[1
]}

Bihlmeier, Angela ^{[2
]}

Wagner, Danny ^{[3
,4
]}

Koelmel, Dominik K. ^{[3
]}

Hoerner, Anna ^{[3
,5
]}

Braese, Stefan ^{[3
,4
]}

Cruz, Carlos H. Brito ^{[1
]}

Padilha, Lazaro A. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Fis Gleb Wataghin, CP 6165, BR-13083970 Campinas, SP, Brazil

[2] Karlsruhe Inst Technol, Inst Phys Chem, D-76131 Karlsruhe, Germany

[3] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[4] Karlsruhe Inst Technol, Inst Toxicol & Genet, D-76344 Eggenstein Leopoldshafen, Germany

[5] Karlsruhe Inst Technol, Light Technol Inst, D-76131 Karlsruhe, Germany

来源：

PHYSICAL CHEMISTRY CHEMICAL PHYSICS | 2017年 / 19卷 / 32期

基金：

巴西圣保罗研究基金会;

关键词：

FLUORESCENT; FLUOROPHORES; SQUARAINE; POLYMETHINE;

D O I：

10.1039/c6cp07849d

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We report on the two-photon absorption spectra of a series of 2,6-disubstituted BODIPY dyes. Depending on the substituents, we observe increasing two-photon absorption cross sections with values up to 350 GM compared to 70 GM in the unsubstituted dye. Quantum chemical calculations are performed to assign the absorption bands and to understand the factors controlling the size of the two-photon absorption cross section. Both the maximum of the two-photon absorption band as well as the red- shift of the whole spectrum correlate with the ability of the substituents to extend the pi-electron system of the dye. The above-mentioned intense two-photon absorption band corresponds to the absorption of photons with 1.3 eV, which is at the first near-infrared transparency window for biological tissues. The dyes could thus be suitable for bio-imaging applications.

引用

页码：21683 / 21690

页数：8

共 35 条

[1]

[Anonymous], 1995, Excited States and Photochemistry of Organic Molecules

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3] Two-Photon Absorption-Related Properties of Functionalized BODIPY Dyes in the Infrared Range up to Telecommunication Wavelengths [J].

Bouit, Pierre-Antoine ;

Kamada, Kenji ;

Feneyrou, Patrick ;

Berginc, Gerard ;

Toupet, Loic ;

Maury, Olivier ;

Androud, Chantal .

ADVANCED MATERIALS, 2009, 21 (10-11) :1151-1154

[4] Differential Many-Body Cooperativity in Electronic Spectra of Oligonuclear Transition-Metal Complexes [J].

Chmela, Jiri ;

Harding, Michael E. ;

Matioszek, Dimitri ;

Anson, Christopher E. ;

Breher, Frank ;

Klopper, Wim .

CHEMPHYSCHEM, 2016, 17 (01) :37-45

[5] Extended squaraine dyes with large two-photon absorption cross-sections [J].

Chung, Sung-Jae ;

Zheng, Shijun ;

Odani, Toru ;

Beverina, Luca ;

Fu, Jie ;

Padilha, Lazaro A. ;

Biesso, Arianna ;

Hales, Joel M. ;

Zhan, Xiaowei ;

Schmidt, Karin ;

Ye, Aijun ;

Zojer, Egbert ;

Barlow, Stephen ;

Hagan, David J. ;

Van Stryland, Eric W. ;

Yi, Yuanping ;

Shuai, Zhigang ;

Pagani, Giorgio A. ;

Bredas, Jean-Luc ;

Perry, Joseph W. ;

Marder, Seth R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (45) :14444-14445

[6] Improved push-pull-push E-Bodipy fluorophores for two-photon cell-imaging [J].

Didier, Pascal ;

Ulrich, Gilles ;

Mely, Yves ;

Ziessel, Raymond .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (18) :3639-3642

[7]

Drobizhev M, 2011, NAT METHODS, V8, P393, DOI [10.1038/NMETH.1596, 10.1038/nmeth.1596]

[8] Molecular structure - two-photon absorption property relations in polymethine dyes [J].

Fu, Jie ;

Padilha, Lazaro A. ;

Hagan, David J. ;

Van Stryland, Eric W. ;

Przhonska, Olga V. ;

Bondar, Mikhail V. ;

Slominsky, Yuriy L. ;

Kachkovski, Alexei D. .

JOURNAL OF THE OPTICAL SOCIETY OF AMERICA B-OPTICAL PHYSICS, 2007, 24 (01) :56-66

[9] Rational design of visible and NIR distyryl-BODIPY dyes from a novel fluorinated platform [J].

Galangau, Olivier ;

Dumas-Verdes, Cecile ;

Meallet-Renault, Rachel ;

Clavier, Gilles .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) :4546-4553

[10] Non-Condon Effects in the One- and Two-Photon Absorption Spectra of the Green Fluorescent Protein [J].

Kamarchik, Eugene ;

Krylov, Anna I. .

JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2011, 2 (05) :488-492

← 1 2 3 4 →