Shuo Li, Zhihao Lu, Shuo Yan, Lijun Mao, Xin Zhang and Da Ma*,
{"title":"杯[n]氮杂二基二苯甲酸酯：分子内氢键辅助合成、酸致变色和定向自组装。","authors":"Shuo Li, Zhihao Lu, Shuo Yan, Lijun Mao, Xin Zhang and Da Ma*, ","doi":"10.1021/acs.orglett.5c03205","DOIUrl":null,"url":null,"abstract":"<p >Here, intramolecular hydrogen bond (IMHBs)-induced rigidity is used for the first time to synthesize macrocyclic arenes. Calix[<i>n</i>]azanediyldibenzoates (C[<i>n</i>]A, where <i>n</i> = 3, 4, or 5) are synthesized through a one-step condensation reaction between dimethyl 2,2′-azanediyldibenzoate and paraformaldehyde. Compared to the monomer, the macrocycles exhibit a fast and significant acidochromic response due to the intramolecular charge transfer that is boosted by the synergistic effect of their adsorption and protonation. In particular, the specific 1,2-alternate conformer of C[4]A allows it to assemble into a one-dimensional channel in a portal to portal mode, which can be used for the oriented assembly of aromatic aldehydes. This study offers a new perspective for designing novel macrocyclic arenes and provides an important supramolecular example for stimulus-responsive materials and manipulating crystal orientation.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 37","pages":"10383–10389"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Calix[n]azanediyldibenzoate: Intramolecular Hydrogen Bond-Assisted Synthesis, Acidichromism, and Oriented Self-Assembly\",\"authors\":\"Shuo Li, Zhihao Lu, Shuo Yan, Lijun Mao, Xin Zhang and Da Ma*, \",\"doi\":\"10.1021/acs.orglett.5c03205\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Here, intramolecular hydrogen bond (IMHBs)-induced rigidity is used for the first time to synthesize macrocyclic arenes. Calix[<i>n</i>]azanediyldibenzoates (C[<i>n</i>]A, where <i>n</i> = 3, 4, or 5) are synthesized through a one-step condensation reaction between dimethyl 2,2′-azanediyldibenzoate and paraformaldehyde. Compared to the monomer, the macrocycles exhibit a fast and significant acidochromic response due to the intramolecular charge transfer that is boosted by the synergistic effect of their adsorption and protonation. In particular, the specific 1,2-alternate conformer of C[4]A allows it to assemble into a one-dimensional channel in a portal to portal mode, which can be used for the oriented assembly of aromatic aldehydes. This study offers a new perspective for designing novel macrocyclic arenes and provides an important supramolecular example for stimulus-responsive materials and manipulating crystal orientation.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 37\",\"pages\":\"10383–10389\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03205\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03205","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Calix[n]azanediyldibenzoate: Intramolecular Hydrogen Bond-Assisted Synthesis, Acidichromism, and Oriented Self-Assembly
Here, intramolecular hydrogen bond (IMHBs)-induced rigidity is used for the first time to synthesize macrocyclic arenes. Calix[n]azanediyldibenzoates (C[n]A, where n = 3, 4, or 5) are synthesized through a one-step condensation reaction between dimethyl 2,2′-azanediyldibenzoate and paraformaldehyde. Compared to the monomer, the macrocycles exhibit a fast and significant acidochromic response due to the intramolecular charge transfer that is boosted by the synergistic effect of their adsorption and protonation. In particular, the specific 1,2-alternate conformer of C[4]A allows it to assemble into a one-dimensional channel in a portal to portal mode, which can be used for the oriented assembly of aromatic aldehydes. This study offers a new perspective for designing novel macrocyclic arenes and provides an important supramolecular example for stimulus-responsive materials and manipulating crystal orientation.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
![Calix[n]azanediyldibenzoate: Intramolecular Hydrogen Bond-Assisted Synthesis, Acidichromism, and Oriented Self-Assembly](https://img.booksci.cn/booksciimg/2025-9/104309386631790456027.jpg)
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
