Novel distyryl BODIPY-fullerene dyads: preparation, characterization and photosensitized singlet oxygen generation efficiency

被引:14
作者
Unlu, Hasan [1 ]
Okutan, Elif [1 ]
机构
[1] Gebze Tech Univ, Dept Chem, Fac Sci, POB 141, TR-41400 Gebze, Kocaeli, Turkey
关键词
ELECTRON-TRANSFER; DYES;
D O I
10.1039/c7nj02010d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Novel types of mono- and bis-distyryl-BODIPY-fullerene dyads, 6 and 7, were prepared by Bingel cyclopropanation. Distyryl-BODIPY derivative (3) was reacted with methyl malonyl chloride and malonyl dichloride respectively for the synthesis of compounds 4 and 5 as light-harvesting antennae that contain one and two BODIPY units. Through the Bingel cyclopropanation of these BODIPYs (4 and 5) with fullerene-C-60 in the presence of CBr4 and DBU, distyryl-BODIPY-fullerene dyads 6 and 7 were obtained. All newly synthesized compounds were characterized by MALDI-MS, H-1 and C-13 NMR and elemental analysis. Moreover, the photophysical and photochemical properties of these heavy atom free dyads were investigated for the determination of their photosensitizer and fluorescence abilities in the near IR region to generate singlet oxygen.
引用
收藏
页码:10424 / 10431
页数:8
相关论文
共 37 条
[1]   Tuning Photosensitized Singlet Oxygen Generation Efficiency of Novel Aza-BODIPY Dyes [J].
Adarsh, Nagappanpillai ;
Avirah, Rekha R. ;
Ramaiah, Danaboyina .
ORGANIC LETTERS, 2010, 12 (24) :5720-5723
[2]   Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy [J].
Awuah, Samuel G. ;
You, Youngjae .
RSC ADVANCES, 2012, 2 (30) :11169-11183
[3]   Exceptional redox and photophysical properties of a triply fused diporphyrin-C60 conjugate:: Novel scaffolds for multicharge storage in molecular scale electronics [J].
Bonifazi, D ;
Scholl, M ;
Song, FY ;
Echegoyen, L ;
Accorsi, G ;
Armaroli, N ;
Diederich, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) :4966-4970
[4]  
Bryce-Smith D., 1977, SPECIALIST PERIODICA, V8
[5]   Designing Excited States: Theory-Guided Access to Efficient Photosensitizers for Photodynamic Action [J].
Cakmak, Yusuf ;
Kolemen, Safacan ;
Duman, Selin ;
Dede, Yavuz ;
Dolen, Yusuf ;
Kilic, Bilal ;
Kostereli, Ziya ;
Yildirim, Leyla Tatar ;
Dogan, A. Lale ;
Guc, Dicle ;
Akkaya, Engin U. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (50) :11937-11941
[6]   Synthesis and photoelectrochemical properties of a fullerene-azothiophene dyad [J].
Cattarin, S ;
Ceroni, P ;
Guldi, DM ;
Maggini, M ;
Menna, E ;
Paolucci, F ;
Roffia, S ;
Scorrano, G .
JOURNAL OF MATERIALS CHEMISTRY, 1999, 9 (11) :2743-2750
[7]   A liquid-crystalline hexa-adduct of [60]fullerene [J].
Chuard, T ;
Deschenaux, R ;
Hirsch, A ;
Schönberger, H .
CHEMICAL COMMUNICATIONS, 1999, (20) :2103-2104
[8]   Covalent fullerene chemistry [J].
Diederich, F ;
Thilgen, C .
SCIENCE, 1996, 271 (5247) :317-323
[9]  
Diekers M, 1998, EUR J ORG CHEM, V1998, P1111, DOI 10.1002/(SICI)1099-0690(199806)1998:6<1111::AID-EJOC1111>3.0.CO
[10]  
2-B