Metal-Free Phthalocyanines Bearing Eight Alkylsulfonyl Substituents: Design, Synthesis, Electronic Structure, and Mesomorphism of New Electron-Deficient Mesogens
作者： Benoît Tylleman , Gabin Gbabode , Claire Amato , Claudine Buess-Herman , Vincent Lemaur
DOI: 10.1021/CM900383C
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摘要: This paper describes the synthesis and physicochemical characterization of novel metal-free phthalocyanines Pc(SO2R)8, bearing eight peripheral alkylsulfonyl substituents. The key synthetic step is efficient eightfold oxidation sulfanyl (SR) into sulfonyl (SO2R) functions in precursor Pc(SR)8. Quantum-chemical calculations show a considerable stabilization HOMO LUMO levels Pc(SO2R)8 as result presence strongly electron-withdrawing groups, while HOMO−LUMO gap remains nearly unaffected. redox behavior electronic spectra were investigated by cyclic voltammetry absorption spectroscopy, respectively, to confirm theoretical predictions. Particularly noteworthy first reduction potential −0.14 V vs saturated calomel electrode (SCE), which falls within empirically established air-stability window for n-type semiconductors. Supramolecular structures mesophases their precursors Pc(SR)8...
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sci-hub.se 参考文章(52)
Sergey Sergeyev, Olivier Debever, Eric Pouzet, Yves Henri Geerts, Transition temperature engineering of octaalkoxycarbonyl phthalocyanines Journal of Materials Chemistry. ,vol. 17, pp. 3002- 3007 ,(2007) , 10.1039/B704344A
Brooks A. Jones, Antonio Facchetti, Michael R. Wasielewski, Tobin J. Marks, Tuning Orbital Energetics in Arylene Diimide Semiconductors. Materials Design for Ambient Stability of n-Type Charge Transport Journal of the American Chemical Society. ,vol. 129, pp. 15259- 15278 ,(2007) , 10.1021/JA075242E
Sandeep Kumar, Self-organization of disc-like molecules: chemical aspects Chemical Society Reviews. ,vol. 35, pp. 83- 109 ,(2006) , 10.1039/B506619K
Gema de la Torre, M. Victoria Martínez-Díaz, Peter R. Ashton, Tomás Torres, Novel Homo- and Heterodimetallic Heterobinuclear Phthalocyaninato-Triazolehemiporphyrazinate Complexes Journal of Organic Chemistry. ,vol. 63, pp. 8888- 8893 ,(1998) , 10.1021/JO981118P
Wojciech Pisula, Marcel Kastler, Daniel Wasserfallen, Mihail Mondeshki, Jorge Piris, Ingo Schnell, Klaus Müllen, Relation between supramolecular order and charge carrier mobility of branched alkyl hexa-peri-hexabenzocoronenes Chemistry of Materials. ,vol. 18, pp. 3634- 3640 ,(2006) , 10.1021/CM0602343
Andrés de la Escosura, M. Victoria Martínez-Díaz, Pall Thordarson, Alan E. Rowan, Roeland J. M. Nolte, Tomás Torres, Donor-acceptor phthalocyanine nanoaggregates. Journal of the American Chemical Society. ,vol. 125, pp. 12300- 12308 ,(2003) , 10.1021/JA030038M
Vincent Lemaur, Demetrio A. da Silva Filho, Veaceslav Coropceanu, Matthias Lehmann, Yves Geerts, Jorge Piris, Michael G. Debije, Anick M. van de Craats, Kittusamy Senthilkumar, Laurens D. A Siebbeles, John M. Warman, Jean-Luc Brédas, Jérôme Cornil, Charge transport properties in discotic liquid crystals: a quantum-chemical insight into structure-property relationships. Journal of the American Chemical Society. ,vol. 126, pp. 3271- 3279 ,(2004) , 10.1021/JA0390956
Stijn De Vusser, Soeren Steudel, Kris Myny, Jan Genoe, Paul Heremans, Low voltage complementary organic inverters Applied Physics Letters. ,vol. 88, pp. 162116- ,(2006) , 10.1063/1.2197604
A. Lux, G.G. Rozenberg, K. Petritsch, S.C. Moratti, A.B. Holmes, R.H. Friend, A series of novel liquid crystalline octakis(alkylthio)-substituted phthalocyanines Synthetic Metals. ,vol. 102, pp. 1527- 1528 ,(1999) , 10.1016/S0379-6779(98)01149-7
Kazuchika Ohta, Hiroshi Hasebe, Hiroshi Ema, Tetsuya Fujimoto, Iwao Yamamoto, π-Acceptors in discotic columnar liquid crystals; an octasubstituted bis(diphenylethane-1,2-dithiol)nickel complex Journal of The Chemical Society, Chemical Communications. pp. 1610- 1611 ,(1989) , 10.1039/C39890001610