Linear and Nonlinear Optical Spectroscopy of Fluoroalkylated BODIPY Dyes

被引：40

作者：

Koelmel, Dominik K. ^{[1
]}

Hoerner, Anna ^{[1
,2
,3
]}

Castaneda, Juan A. ^{[2
]}

Ferencz, Julio A. P. ^{[2
]}

Bihlmeier, Angela ^{[4
]}

Nieger, Martin ^{[5
]}

Braese, Stefan ^{[1
,6
]}

Padilha, Lazaro A. ^{[2
]}

机构：

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

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

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

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

[5] Univ Helsinki, Inorgan Chem Lab, POB 55, FIN-00014 Helsinki, Finland

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

来源：

JOURNAL OF PHYSICAL CHEMISTRY C | 2016年 / 120卷 / 08期

基金：

巴西圣保罗研究基金会;

关键词：

TUNABLE FLUORESCENT DYES; EXCITED-STATE ABSORPTION; EFFICIENT SYNTHESIS; SINGLET OXYGEN; DERIVATIVES; ENHANCEMENT; PYRROLE; BRIGHT; PROBES; SERIES;

D O I：

10.1021/acs.jpcc.6b00096

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：

A series of fluoroalkyl-labeled BODIPY dyes have been synthesized with different substituents on the 2- and 6-positions and investigated in terms of their spectroscopic properties. The dyes were decorated with aryl, alkenyl, and alkynyl substituents, respectively. Those substituents are able to expend the dyes' delocalized pi-electron system to different extents. Detailed linear and nonlinear optical spectroscopy methods as well as quantum-chemical calculations have been employed to verify the influence of those different substituents on the electronic distribution and, ultimately, on the molecules' optical properties. From the nonlinear optical measurements, we find that the substituents highly influence the excited-state absorption properties, which could be tuned in wavelength by similar to 100 nm and in magnitude by over 1 order of magnitude, reaching peak values close to 10(-15) cm(2) for one of the alkynyl-containing dyes.

引用

页码：4538 / 4545

页数：8

共 50 条

[1]

[Anonymous], 1989, PROGR PACK AB IN EL

[2] Synthesis and photo-physical properties of a series of BODIPY dyes [J].

Banfi, Stefano ;

Nasini, Gianluca ;

Zaza, Stefano ;

Caruso, Enrico .

TETRAHEDRON, 2013, 69 (24) :4845-4856

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

BECKE, AD .

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

[4] Fluorescent indicators based on BODIPY [J].

Boens, Noel ;

Leen, Volker ;

Dehaen, Wim .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172

[5] PHOTOPROCESSES IN DIPHENYLPOLYENES - OXYGEN AND HEAVY-ATOM ENHANCEMENT OF TRIPLET YIELDS [J].

CHATTOPADHYAY, SK ;

DAS, PK ;

HUG, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4507-4514

[6] 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

[7] Donor-Acceptor-Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission [J].

Ellinger, Stefan ;

Graham, Kenneth R. ;

Shi, Pengjie ;

Farley, Richard T. ;

Steckler, Timothy T. ;

Brookins, Robert N. ;

Taranekar, Prasad ;

Mei, Jianguo ;

Padilha, Lazaro A. ;

Ensley, Trenton R. ;

Hu, Honghua ;

Webster, Scott ;

Hagan, David J. ;

Van Stryland, Eric W. ;

Schanze, Kirk S. ;

Reynolds, John R. .

CHEMISTRY OF MATERIALS, 2011, 23 (17) :3805-3817

[8] Shining Light on the Dark Side of Imaging: Excited State Absorption Enhancement of a Bis-styryl BODIPY Photoacoustic Contrast Agent [J].

Frenette, Mathieu ;

Hatamimoslehabadi, Maryam ;

Bellinger-Buckley, Stephanie ;

Laoui, Samir ;

La, Jeffrey ;

Bag, Seema ;

Mallidi, Srivalleesha ;

Hasan, Tayyaba ;

Bouma, Brett ;

Yeleswarapu, Chandra ;

Rochford, Jonathan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15853-15856

[9] 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

[10] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe [J].

Gabe, Y ;

Urano, Y ;

Kikuchi, K ;

Kojima, H ;

Nagano, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3357-3367

← 1 2 3 4 5 →