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Chem."],"abstract":"<jats:p>Several new chiral pillar[4]arene[1]quinone derivatives were synthesized by reacting pillar[4]arene[1]quinone (<jats:bold>EtP4Q1<\/jats:bold>), containing four 1,4-diethoxybenzene units and one benzoquinone unit, with various chiral amines <jats:italic>via<\/jats:italic> Michael addition. Due to the direct introduction of chiral substituents on the rim of pillar[n]arene and the close location of the chiral center to the rim of <jats:bold>EtP4Q1<\/jats:bold>, the newly prepared compounds showed unique chiroptical properties without complicated chiral resolution processes, and unprecedented high anisotropy factor of up to \u22120.018 at the charge transfer absorption band was observed. Intriguingly, the benzene sidearm attached pillar[4]arene[1]quinone derivative <jats:bold>1a<\/jats:bold> showed solvent- and complexation-driven chirality inversion. This work provides a promising potential for absolute asymmetric synthesis of pillararene-based derivatives.<\/jats:p>","DOI":"10.3389\/fchem.2021.713305","type":"journal-article","created":{"date-parts":[[2021,7,7]],"date-time":"2021-07-07T06:29:28Z","timestamp":1625639368000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":10,"title":["Solvent-Driven Chirality Switching of a Pillar[4]arene[1]quinone Having a Chiral Amine-Substituted Quinone Subunit"],"prefix":"10.3389","volume":"9","author":[{"given":"Chunhong","family":"Liu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhipeng","family":"Yu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiabin","family":"Yao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiecheng","family":"Ji","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting","family":"Zhao","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wanhua","family":"Wu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2021,7,7]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"5629","DOI":"10.3390\/molecules15085629","article-title":"Synthesis and Biological Evaluation of 2,5-Bis(alkylamino)-1,4-Benzoquinones","volume":"15","author":"Almeida Barbosa","year":"2010","journal-title":"Molecules"},{"key":"B2","doi-asserted-by":"publisher","first-page":"1746","DOI":"10.1002\/anie.200250524","article-title":"Solid-State Supramolecular Chirogenesis: High Optical Activity and Gradual Development of Zinc Octaethylporphyrin Aggregates","volume":"42","author":"Borovkov","year":"","journal-title":"Angew. 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