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Home  >  Journal list  >  Polymer Journal  >  Vol.49  No.1 (2017)  >  pp.189-195

Polymer Journal
<<Previous article Vol.49  No.1 (2017)   pp.189 - 195 Next article>>

Supramolecular polymerization of hydrogen-bonded rosettes with anthracene chromophores: regioisomeric effect on nanostructures

Deepak D Prabhu1, Keisuke Aratsu1, Mitsuaki Yamauchi1, Xu Lin1, Bimalendu Adhikari1 and Shiki Yagai1
1Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Chiba, Japan

Two regioisomeric barbituric acid compounds possessing (phenylethynyl) anthracene cores and tridodecyloxy phenyl units were synthesized. UV–Vis spectroscopic studies showed that the two compounds self-assemble by a cooperative mechanism in methylcyclohexane (MCH) with different stacking arrangements of the π-conjugated core, which leads to distinct aggregation-induced color changes. Atomic Force Microscopic studies revealed the formation of well-defined fibrous supramolecular polymers with different topological features, that is, cylindrical or helically twisted shapes. For the helically twisted supramolecular polymer, adding small amounts of limonene as a cosolvent induced more pronounced changes in absorption, which indicated an increased ππ stacking interaction in the cosolvent system compared with that in pure MCH. Molecular modeling studies suggested that the two molecules form supramolecular polymers by forming hydrogen-bonded hexameric supermacrocycles (rosettes) and that different twisting angles of the anthracene chromophore with respect to the barbituric acid plane can explain the observed difference in spectroscopic and morphological properties.

Received: July 15, 2016 , Revised: August 23, 2016
Accepted: August 25, 2016 , Published online: October 19, 2016
© 2017 The Society of Polymer Science, Japan

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