Solvent mediated thermodynamically favorable helical supramolecular self-assembly: recognition behavior towards achiral and chiral analytes

Meenal Kataria; Youngseo Kim; Hong Diem Chau; Na Yeon Kwon; Yongju Hong; Taekyung Kim; Jaewan Ko; Myung Kook Son; Joona Bang; Sungnam Park; Hugh I. Kim; Kwangyeol Lee; Dong Hoon Choi

doi:10.1039/D2TC01113A

Solvent mediated thermodynamically favorable helical supramolecular self-assembly: recognition behavior towards achiral and chiral analytes†

Meenal Kataria,^a Youngseo Kim,^a Hong Diem Chau,

^a Na Yeon Kwon,^a Yongju Hong,^a Taekyung Kim,^b Jaewan Ko,^c Myung Kook Son,^d Joona Bang,

^c Sungnam Park,

^a Hugh I. Kim,

^d Kwangyeol Lee

^a and Dong Hoon Choi

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Research Institute for Natural Sciences, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul, Republic of Korea
E-mail: dhchoi8803@korea.ac.kr

^b Korea Basic Science Institute, 145 Anam-ro, Seongbuk-gu, Seoul, Korea

^c Department of Chemical and Bioengineering, Korea University, Seoul, Republic of Korea

^d Department of Chemistry, Korea University, Seoul, Republic of Korea

Abstract

Herein, we successfully developed an entropically favored helical supramolecular self-assembly from a triphenylamine-based derivative 4 in a green solvent in order to mimic the structural transformations that occur during the self-assembly of proteins/peptides which may cause various neurodegenerative diseases. Its structural transformation from helical supramolecular self-assembly to a random coil and then achiral nanorods was studied by varying the concentration of achiral stimuli (i.e., Fe²⁺ ions). The driving force of this transformation is the strong binding affinity of chiral supramolecular assemblies and Fe²⁺ ions. Furthermore, the “metal-free” helical supramolecular self-assembly exhibited enantioselectivity for differentiating between L- and D-proline; this was achieved through a chiral stimuli-induced structural modulation methodology. Our evaluation of the effects of achiral/chiral stimuli is also novel.

Journal of Materials Chemistry C

Solvent mediated thermodynamically favorable helical supramolecular self-assembly: recognition behavior towards achiral and chiral analytes†

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Solvent mediated thermodynamically favorable helical supramolecular self-assembly: recognition behavior towards achiral and chiral analytes

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