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Design of an Amphiphilic Perylene Diimide for Optical Recognition of Anticancer Drug through a Chirality‐Induced Helical Structure
Author(s) -
Zhao Hao,
Hussain Sameer,
Liu Xiaoyan,
Li Shengliang,
Lv Fengting,
Liu Libing,
Wang Shu
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901948
Subject(s) - perylene , chirality (physics) , supramolecular chirality , diimide , stacking , supramolecular chemistry , molecular recognition , amphiphile , hydrogen bond , chemistry , chromophore , supramolecular assembly , stereochemistry , covalent bond , molecule , photochemistry , organic chemistry , polymer , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , copolymer , quark
of chirality into a supramolecular self‐assembly system plays an indispensable role in attaining specific molecular recognition ability. Herein, a chiral anticancer drug 5′‐deoxy‐5‐fluorouridine (5′DFU) was explored for inducing the self‐assembly of a cationic perylene diimide derivative containing boronic acid groups (PDI‐PBA) into a highly ordered right‐handed helical structure. As a result, PDI‐PBA exhibited a molecular recognition ability towards 5′DFU among other cis ‐diols and anticancer drugs. With the help of a dynamic covalent bond and favorable hydrogen‐bonding interactions, chirality transfer from chiral 5′DFU to achiral PDI‐PBA breaks down the strong π–π stacking of PDI‐PBA and makes it reorganize into highly ordered helical supramolecular structures. This work provides an insight into chiral anticancer drug tuning interactions of π‐chromophores and the inducement of hierarchical self‐assembly to achieve specific molecular recognition.