Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit
Open Access
- 7 July 2021
- journal article
- research article
- Published by Frontiers Media SA in Frontiers in Chemistry
Abstract
Several new chiral pillar[4]arene[1]quinone derivatives were synthesized by reacting pillar[4]arene[1]quinone (EtP4Q1), containing four 1,4-diethoxybenzene units and one benzoquinone unit, with various chiral amines via Michael addition. The chirally modified pillar[4]arene[1]quinons showed unique chiroptical properties, giving anisotropy factors of the charge transfer up to -0.018. Intriguingly, the chiroptical properties could be switched by the use of different solvents.Keywords
Funding Information
- National Natural Science Foundation of China (92056116 21871194 21971169 21572142)
- National Key Research and Development Program of China (2017YFA0505903)
- Department of Science and Technology of Sichuan Province (2019YJ0160 2019YJ0090 2017SZ0021)
- Fundamental Research Funds for the Central Universities (20826041D4117)
This publication has 67 references indexed in Scilit:
- Competitive Selection of Conformation Chirality of Water-Soluble Pillar[5]arene Induced by Amino Acid DerivativesOrganic Letters, 2020
- Chemical On/Off Switching of Mechanically Planar Chirality and Chiral Anion Recognition in a [2]Rotaxane Molecular ShuttleJournal of the American Chemical Society, 2019
- Enhanced Triplet–Triplet Energy Transfer and Upconversion Fluorescence through Host–Guest ComplexationJournal of the American Chemical Society, 2016
- Conformational photoswitching of a synthetic peptide foldamer bound within a phospholipid bilayerScience, 2016
- Optical chirality sensing using macrocycles, synthetic and supramolecular oligomers/polymers, and nanoparticle based sensorsChemical Society Reviews, 2015
- Chiral Selective Transmembrane Transport of Amino Acids through Artificial ChannelsJournal of the American Chemical Society, 2013
- Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-benzoquinonesMolecules, 2010
- Chiral transfer in coordination complexes: towards molecular materialsChemical Society Reviews, 2009
- The Origin of Solvent‐Controlled Supramolecular Chirality Switching in a Bis(Zinc Porphyrin) SystemAngewandte Chemie, 2003
- Solid‐State Supramolecular Chirogenesis: High Optical Activity and Gradual Development of Zinc Octaethylporphyrin AggregatesAngewandte Chemie, 2003