Self-assembly constructed by perylene bisimide derivatives bearing complementary hydrogen-bonding moieties

作者: Xin-guo Yang , Huan Yuan , Qiu-li Zhao , Qing Yang , Xian-hong Chen

DOI: 10.1007/S11771-009-0035-1

关键词:

摘要: An intermediate compound 2, 4-bis(laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring lauryl amine and subsequently 1-(2-aminoethyl)-piperazine. Then imidization of perylene-3, 4, 9, 10-tetracarboxylic acid dianhydride with 2,4-bis(laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, carried out to afford a novel perylene derivative bearing two melamine blocks (S2) 1, 6, 7, 12-tetra(4-tert-butyl phenoxy)-perylene-3, bisimide (S1). The hydrogen-bonding interactions between S1 S2 were investigated 1H NMR spectrum, UV/Vis spectrum fluorescence spectrum. influences the morphologies S1·S2 aggregates investigated. results show that well-defined nanofibers diameter about 100 nm can be obtained self-assembly only in CH2Cl2 solution. Based these results, guidelines for molecular design supramolecular polymer materials are presented.

参考文章(21)
Shiki Yagai, Masatsugu Higashi, Takashi Karatsu, Akihide Kitamura, Binary supramolecular gels based on bismelamine.cyanurate/barbiturate noncovalent polymers Chemistry of Materials. ,vol. 16, pp. 3582- 3585 ,(2004) , 10.1021/CM048963A
Jian Zhang, Freek J. M. Hoeben, Maarten J. Pouderoijen, Albertus P. H. J. Schenning, E. W. Meijer, Frans C. De Schryver, Steven De Feyter, Hydrogen‐Bonded Oligo(p‐phenylenevinylene) Functionalized with Perylene Bisimide: Self‐Assembly and Energy Transfer Chemistry: A European Journal. ,vol. 12, pp. 9046- 9055 ,(2006) , 10.1002/CHEM.200600651
Frank Würthner, Christoph Thalacker, Armin Sautter, Wolfgang Schärtl, Wolfram Ibach, Olaf Hollricher, Hierarchical Self‐Organization of Perylene Bisimide–Melamine Assemblies to Fluorescent Mesoscopic Superstructures Chemistry: A European Journal. ,vol. 6, pp. 3871- 3886 ,(2000) , 10.1002/1521-3765(20001103)6:21<3871::AID-CHEM3871>3.3.CO;2-W
Frank Würthner, Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures Chemical Communications. ,vol. 2004, pp. 1564- 1579 ,(2004) , 10.1039/B401630K
Steven De Feyter, Atsushi Miura, Sheng Yao, Zhijian Chen, Frank Würthner, Pascal Jonkheijm, Albertus P. H. J. Schenning, E. W. Meijer, Frans C. De Schryver, Two-Dimensional Self-Assembly into Multicomponent Hydrogen-Bonded Nanostructures Nano Letters. ,vol. 5, pp. 77- 81 ,(2005) , 10.1021/NL048360Y
Xin-Guo Yang, Jing-Zhi Sun, Han-Ying Li, Mang Wang, Jian Cao, Fluorescence Switch Based on a Porphyrin-perylene Dyad Chinese Chemical Letters. ,vol. 16, pp. 257- 260 ,(2005)
Freek J. M. Hoeben, Pascal Jonkheijm, E. W. Meijer, Albertus P. H. J. Schenning, About Supramolecular Assemblies of π-Conjugated Systems Chemical Reviews. ,vol. 105, pp. 1491- 1546 ,(2005) , 10.1021/CR030070Z
Yanfeng Wang, Yanli Chen, Renjie Li, Shuangqing Wang, Wei Su, Pan Ma, Michael R. Wasielewski, Xiyou Li, Jianzhuang Jiang, Amphiphilic perylenetretracarboxyl diimide dimer and its application in field effect transistor. Langmuir. ,vol. 23, pp. 5836- 5842 ,(2007) , 10.1021/LA063729F