Nanostructuration of phenylenevinylenediimide-bridged silsesquioxane: From electroluminescent molecular J-aggregates to photoresponsive polymeric H-aggregates

被引:75
作者
Dautel, OJ
Wantz, G
Almairac, R
Flot, D
Hirsch, L
Lere-Porte, JP
Parneix, JP
Serein-Spirau, F
Vignau, L
Moreau, JJE
机构
[1] Ecole Natl Super Chim Montpellier, CNRS, Heterochim Mol & Macromol UMR 5076, F-34296 Montpellier, France
[2] Ecole Natl Super Chim & Phys Bordeaux, Federat Rech, CNRS, FR 2648,Labs PIOM & IXL, F-33607 Pessac, France
[3] Univ Montpellier 2, UMR 5587, LCVN, F-34095 Montpellier, France
[4] European Mol Biol Lab, F-38042 Grenoble 9, France
关键词
D O I
10.1021/ja058680z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new approach to control molecular aggregation of pi-conjugated chromophores in the solid state has been investigated. Our strategy was to use a modifiable bulky fragment which should induce a J-aggregation and offer the possibility to reach an H-aggregation upon its chemical modification by lateral slip of T-conjugated molecules. The chosen fragment for that purpose was the hydrolyzable triethoxysilane function (Si(OEt)(3)). Our objective was to design and synthesize electroluminescent or solar cell hybrid organic-inorganic materials by the sol-gel process applied to a bifunctionalized silane. With this intention, the synthesis of the sol-gel processable phenylenevinylenediimide silsesquioxane 6 was accomplished and the study of spin-coated thin films of the pure silane precursor subjected or not to the sol-gel process has been carried out. Optical properties of 6 are consistent with the formation of J-aggregates in the solid state due to the steric hindrance introduced by the triethoxysilane units. Conversely, the spectroscopic behavior observed for the hybrid film 6F is attributed to an H-aggregation corresponding to a "card pack" orientation of the distyrylbenzeneimide chromophores in the compressed silicate network. Morevover, 6 and 6F also exhibited different electronic behaviors: light-emitting diodes exhibited high brightness with the native precursor 6 and almost no light output with the sol-gel processed silsesquioxane 6F. Photovoltaic cells showed the opposite behavior with low photocurrent generation in the precursor case and higher photocurrents with the sol-gel processed layers. These results provide a deeper understanding of the present self-assembly process that is strongly governed by the molecular packing of the oligosiloxane precursor.
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收藏
页码:4892 / 4901
页数:10
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