Synthesis of Symmetrical Multichromophoric Bodipy Dyes and Their Facile Transformation into Energy Transfer Cassettes

被引：67

作者：

Bozdemir, O. Altan ^{[1
]}

Cakmak, Yusuf ^{[1
]}

Sozmen, Fazli ^{[2
]}

Ozdemir, Tugba ^{[1
]}

Siemiarczuk, Aleksander ^{[3
]}

Akkaya, Engin U. ^{[1
,4
]}

机构：

[1] Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

[2] Akdeniz Univ, Fac Arts & Sci, Dept Chem, TR-07058 Antalya, Turkey

[3] PTI Fast Kinet Lab, London, ON N6E 2S8, Canada

[4] Bilkent Univ, Dept Chem, TR-06800 Ankara, Turkey

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 21期

关键词：

dyes/pigments; energy transfer; fluorescence spectroscopy; fluorophores; Sonogashira coupling; HIGHLY EFFICIENT; DISTYRYL-BORADIAZAINDACENES; FLUORESCENT-PROBE; BORON; FUNCTIONALIZATION; CHEMOSENSOR; MODULATION; CHEMISTRY; EMISSION; LIBRARY;

D O I：

10.1002/chem.200903449

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Multichromophoric boron-di-pyrromethene (Bodipy) dyes synthesized on phenylene-ethynylene platforms have been be converted to energy transfer cassettes in a one-step chemical transformation. Excitation energy transfer processes in these highly symmetrical derivatives were studied in detail, including time-resolved fluorescence spectroscopy techniques. Excitation spectra and the emission lifetimes suggest efficient energy transfer between the donor and acceptor chromophore. These novel energy transfer cassettes, while highlighting a short-cut approach to similar energy transfer systems, could be useful as large pseudo-Stokes shift multichromophoric dyes with potential applications in diverse applications.

引用

页码：6346 / 6351

页数：6

共 57 条

[21] Design Strategies for Ratiometric Chemosensors: Modulation of Excitation Energy Transfer at the Energy Donor Site [J].

Guliyev, Ruslan ;

Coskun, Ali ;

Akkaya, Engin U. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :9007-9013

[22] 3- and 5-Functionalized BODIPYs via the Liebeskind-Srogl reaction [J].

Han, Junyan ;

Gonzalez, Oswaldo ;

Aguilar-Aguilar, Angelica ;

Pena-Cabrera, Eduardo ;

Burgess, Kevin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (01) :34-36

[23] Rapid energy transfer in cascade-type bodipy dyes [J].

Harriman, Anthony ;

Izzet, Guillaume ;

Ziessel, Raymond .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10868-10875

[24] Energy Flow in a Purpose-Built Cascade Molecule Bearing Three Distinct Chromophores Attached to the Terminal Acceptor [J].

Harriman, Anthony ;

Mallon, Laura ;

Ziessel, Raymond .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (36) :11461-11473

[25] Charge separation in a nonfluorescent donor-acceptor dyad derived from boron dipyrromethene dye, leading to photocurrent generation [J].

Hattori, S ;

Ohkubo, K ;

Urano, Y ;

Sunahara, H ;

Nagano, T ;

Wada, Y ;

Tkachenko, NV ;

Lemmetyinen, H ;

Fukuzumi, S .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (32) :15368-15375

[26] A BODIPY boronium cation for the sensing of fluoride ions [J].

Hudnall, Todd W. ;

Gabbai, Francois P. .

CHEMICAL COMMUNICATIONS, 2008, (38) :4596-4597

[27] Structural control of the photodynamics of boron-dipyrrin complexes [J].

Kee, HL ;

Kirmaier, C ;

Yu, LH ;

Thamyongkit, P ;

Youngblood, WJ ;

Calder, ME ;

Ramos, L ;

Noll, BC ;

Bocian, DF ;

Scheidt, WR ;

Birge, RR ;

Lindsey, JS ;

Holten, D .

JOURNAL OF PHYSICAL CHEMISTRY B, 2005, 109 (43) :20433-20443

[28] FerriBRIGHT: A Rationally Designed Fluorescent Probe for Redox Active Metals [J].

Kennedy, Daniel P. ;

Kormos, Chad M. ;

Burdette, Shawn C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) :8578-8586

[29] Synthesis of a BODIPY Library and Its Application to the Development of Live Cell Glucagon Imaging Probe [J].

Lee, Jun-Seok ;

Kang, Nam-young ;

Kim, Yun Kyung ;

Samanta, Animesh ;

Feng, Suihan ;

Kim, Hyeong Kyu ;

Vendrell, Marc ;

Park, Jung Hwan ;

Chang, Young-Tae .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (29) :10077-10082

[30] Synthesis and characterization of organoplatinum dendrimers with 1,3,5-triethynylbenzene building blocks [J].

Leininger, S ;

Stang, PJ ;

Huang, SP .

ORGANOMETALLICS, 1998, 17 (18) :3981-3987

← 1 2 3 4 5 6 →