Core-Extended Terrylene Diimide on the Bay Region: Synthesis and Optical and Electrochemical Properties

被引:24
作者
Bai, Qianqian [1 ]
Gao, Baoxiang [1 ,2 ]
Ai, Qi [1 ]
Wu, Yonggang [1 ,2 ]
Ba, Xinwu [1 ,2 ]
机构
[1] Hebei Univ, Coll Chem & Environm Sci, Baoding 071002, Peoples R China
[2] Hebei Univ, Minist Educ, Key Lab Med Chem & Mol Diag, Baoding 071002, Peoples R China
基金
中国国家自然科学基金;
关键词
PERYLENE BISIMIDE DYES; POLYCYCLIC AROMATIC-HYDROCARBONS; CRYSTALLINE CORONENE DERIVATIVES; HEXA-PERI-HEXABENZOCORONENES; FLUORESCENT DYES; BUILDING-BLOCKS; RYLENE DYES; PI-STACKS; TETRACARBOXDIIMIDES; ACENE;
D O I
10.1021/ol202775b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel core-extended terrylene diimides on the bay region (CETDIs) were synthesized via annulation of the four additional ethylene units or benzene units on the bay region of the terrylene diimide core. The optical and electrochemical properties of the two compounds were investigated. These CETDIs exhibited broad absorption spectra with high extinction coefficients, which span a wide range in the ultraviolet and visible spectrum from 300 to 700 nm. Furthermore, the redox process of the CETDIs increased from two waves to four waves, and the lowest unoccupied molecular orbital (LUMO) levels were enhanced from -4.00 to -3.59 eV.
引用
收藏
页码:6484 / 6487
页数:4
相关论文
共 60 条
[11]   Helical growth of semiconducting columnar dye assemblies based on chiral perylene bisimides [J].
Dehm, Volker ;
Chen, Zhijian ;
Baumeister, Ute ;
Prins, Paulette ;
Siebbeles, Laurens D. A. ;
Wuerthner, Frank .
ORGANIC LETTERS, 2007, 9 (06) :1085-1088
[12]   VERY SOLUBLE AND PHOTOSTABLE PERYLENE FLUORESCENT DYES [J].
DEMMIG, S ;
LANGHALS, H .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (02) :225-230
[13]   Core-Extended Terrylene Tetracarboxdiimide: Synthesis and Chiroptical Characterization [J].
Eversloh, Christian Luetke ;
Liu, Zhihong ;
Mueller, Beate ;
Stangl, Michael ;
Li, Chen ;
Muellen, Klaus .
ORGANIC LETTERS, 2011, 13 (20) :5528-5531
[14]   Core-Extended Perylene Tetracarboxdiimides: The Homologous Series of Coronene Tetracarboxdiimides [J].
Eversloh, Christian Luetke ;
Li, Chen ;
Muellen, Klaus .
ORGANIC LETTERS, 2011, 13 (15) :4148-4150
[15]   Hexa-peri-hexabenzocoronenes by efficient oxidative cyclodehydrogenation:: The role of the oligophenylene precursors [J].
Feng, XL ;
Wu, JS ;
Enkelmann, V ;
Mullen, K .
ORGANIC LETTERS, 2006, 8 (06) :1145-1148
[16]   New hydrosoluble perylene and coronene derivatives [J].
Franceschin, M ;
Alvino, A ;
Ortaggi, G ;
Bianco, A .
TETRAHEDRON LETTERS, 2004, 45 (49) :9015-9020
[17]   Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors [J].
Franceschin, Marco ;
Alvino, Antonello ;
Casagrande, Valentina ;
Mauriello, Clementina ;
Pascucci, Emanuela ;
Savino, Maria ;
Ortaggi, Giancarlo ;
Bianco, Armandodoriano .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1848-1858
[18]   Energy Transfer Pathways in a Rylene-Based Triad [J].
Fron, Eduard ;
Puhl, Larissa ;
Oesterling, Ingo ;
Li, Chen ;
Muellen, Klaus ;
De Schryver, Frans C. ;
Hofkens, Johan ;
Vosch, Tom .
CHEMPHYSCHEM, 2011, 12 (03) :595-608
[19]   Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings [J].
Gao, Baoxiang ;
Wang, Ming ;
Cheng, Yanxiang ;
Wang, Lixiang ;
Jing, Xiabin ;
Wang, Fosong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) :8297-8306
[20]   Helical columnar liquid crystals based on dendritic peptides substituted perylene bisimides [J].
Gao, Baoxiang ;
Xia, Defang ;
Zhang, Licui ;
Bai, Qianqian ;
Bai, Libin ;
Yang, Tao ;
Ba, Xinwu .
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (40) :15975-15980