Effect Of C12H25O– Substituent Position On The Self-assembly ...

Effect of C12H25O– substituent position on the self-assembly behaviour of C6H5COO–Ala–Ala dipeptide†

Shuwei Lin, *a Qiyun Tong,b Pan Jiang,b Baozong Li,b Yi Li b and Yonggang Yang *b Author affiliations

* Corresponding authors

a Key Lab of Advanced Optical Manufacturing Technologies of Jiangsu Province & Key Lab of Modern Optical Technologies of Education Ministry of China, School of Optoelectronics Science and Engineering, Soochow University, Suzhou 215123, China E-mail: [email protected], [email protected] Fax: +86 65882052 Tel: +86 65880047

b State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China

Abstract

Three dipeptides based on the Ala–Ala building block with different substituent positions of the dodecyloxy group on the benzoyl residue at the N terminus were designed and synthesized (ortho-, meta- and para-16). All of them were able to spontaneously self-assemble in the mixed solvent of methanol and water (6/4, v/v). However, three dipeptides underwent a distinct kinetically controlled self-assembling process. The spectroscopic study also revealed that, for ortho-16, the phenylene groups and the peptide sequence loosely packed, while meta- and para-16 stacked into well-ordered structures with the formation of parallel β-sheets through supramolecular self-assembly. Intramolecular hydrogen bonding and steric hindrance of the dodecyloxy side chain were proposed to lead to the different self-assembling behaviour of the three isomers.

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