α-/β-Formylated Boron-Dipyrrin (BODIPY) Dyes: Regioselective Syntheses and Photophysical Properties

被引：88
作者：
Yu, Changjiang [1 ,2 ]
Jiao, Lijuan [1 ,2 ]
Yin, Hao [3 ]
Zhou, Jinyuan [1 ,2 ]
Pang, Weidong [1 ,2 ]
Wu, Yangchun [1 ,2 ]
Wang, Zhaoyun [1 ,2 ]
Yang, Gaosheng [1 ,2 ]
Hao, Erhong [1 ,2 ]
机构：
[1] Anhui Normal Univ, Lab Functionalized Mol Solids, Minist Educ, Wuhu 241000, Peoples R China
[2] Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Mol Based Mat, Wuhu 241000, Peoples R China
[3] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 28期
关键词：
BODIPY; Fluorescence; Dyes; pigments; Synthetic methods; EFFICIENT ENERGY-TRANSFER; TUNABLE FLUORESCENT DYES; SPECTRAL PROPERTIES; VILSMEIER FORMYLATION; QUINAZOLINIUM SALTS; TERT-ANILINES; IN-VITRO; FUNCTIONALIZATION; DERIVATIVES; SENSOR;
D O I：
10.1002/ejoc.201100736
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Formylation has been performed on pyrrole-unsubstituted dipyrromethanes 1 and boron-dipyrrin (BODIPY) dyes 4 based on a Vilsmeier-Haack reaction. It is highly regioselective and complementary and occurs exclusively at the alpha- and beta-position, respectively, for pyrrole-unsubstituted dipyrromethanes 1 and BODIPY dyes 4. This regioselective formylation enables the syntheses of a variety of alpha- and beta-substituted BODIPY dyes. The installation of formyl groups affects the electronic properties of the BODIPY chromophore, resulting in red-and blueshifts of the absorption and emission maxima, respectively, for the alpha- and beta-formylated BODIPYs 3 and 5.
引用
收藏
页码：5460 / 5468
页数：9
相关论文
共 97 条
[1]   The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System [J].
Arroyo, Ismael J. ;
Hu, Rongrong ;
Merino, Gabriel ;
Tang, Ben Zhong ;
Pena-Cabrera, Eduardo .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5719-5722
[2]   Water soluble distyryl-boradiazaindacenes as efficient photosensitizers for photodynamic therapy [J].
Atilgan, Serdar ;
Ekmekci, Zeynep ;
Dogan, A. Lale ;
Guc, Dicle ;
Akkaya, Engin U. .
CHEMICAL COMMUNICATIONS, 2006, (42) :4398-4400
[3]   8-PropargylaminoBODIPY: unprecedented blue-emitting pyrromethene dye. Synthesis, photophysics and laser properties [J].
Azael Gomez-Duran, C. F. ;
Garcia-Moreno, Inmaculada ;
Costela, Angel ;
Martin, Virginia ;
Sastre, Roberto ;
Banuelos, Jorge ;
Lopez Arbeloa, Fernando ;
Lopez Arbeloa, Inigo ;
Pena-Cabrera, Eduardo .
CHEMICAL COMMUNICATIONS, 2010, 46 (28) :5103-5105
[4]  
Banuelos-Prieto J., 2010, CHEM-EUR J, V16
[5]   BODIPY-based hydroxyaryl derivatives as fluorescent pH probes [J].
Baruah, M ;
Qin, WW ;
Basaric, N ;
De Borggraeve, WM ;
Boens, N .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4152-4157
[6]   Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution [J].
Baruah, Mukulesh ;
Qin, Wenwu ;
Flors, Cristina ;
Hofkens, Johan ;
Valle, Renaud A. L. ;
Beljonne, David ;
Van der Auweraer, Mark ;
De Borggraeve, Wim M. ;
Boens, Noel .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (18) :5998-6009
[7]   Cofacial Boron Dipyrromethene (Bodipy) Dimers: Synthesis, Charge Delocalization, and Exciton Coupling [J].
Benniston, Andrew C. ;
Copley, Graeme ;
Harriman, Anthony ;
Howgego, David ;
Harrington, Ross W. ;
Clegg, William .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (06) :2018-2027
[8]   Selective Manipulation of ICT and PET Processes in Styryl-Bodipy Derivatives: Applications in Molecular Logic and Fluorescence Sensing of Metal Ions [J].
Bozdemir, O. Altan ;
Guliyev, Ruslan ;
Buyukcakir, Onur ;
Selcuk, Sencer ;
Kolemen, Safacan ;
Gulseren, Gulcihan ;
Nalbantoglu, Tugrul ;
Boyaci, Hande ;
Akkaya, Engin U. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :8029-8036
[9]   Reaction-Based Sensing of Fluoride Ions Using Built-in Triggers for Intramolecular Charge Transfer and Photoinduced Electron Transfer [J].
Bozdemir, O. Altan ;
Sozmen, Fazli ;
Buyukcakir, Onur ;
Guliyev, Ruslan ;
Cakmak, Yusuf ;
Akkaya, Engin U. .
ORGANIC LETTERS, 2010, 12 (07) :1400-1403
[10]  
Brückner C, 1998, J PORPHYR PHTHALOCYA, V2, P455, DOI 10.1002/(SICI)1099-1409(199811/12)2:6<455::AID-JPP67>3.0.CO
12345678910