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One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB2...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5535066/ https://www.ncbi.nlm.nih.gov/pubmed/28808537 http://dx.doi.org/10.1039/c5sc04844c |
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author | Fu, Xin Zhang, Qi Rao, Si-Jia Qu, Da-Hui Tian, He |
author_facet | Fu, Xin Zhang, Qi Rao, Si-Jia Qu, Da-Hui Tian, He |
author_sort | Fu, Xin |
collection | PubMed |
description | The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB24C8) based [c2]daisy chain structure and is ended with a benzo-21-crown-7 (B21C7) based rotaxane at each side. The key to the design involved encoding the selective threading using a steric hindrance-related “language”, where highly selective self-assemblies occurred in a three-component self-sorting process, which included the threading of a benzylalkylammonium into a B21C7 and interpenetrated dimerized formation of a DB24C8 based [c2]daisy chain simultaneously; the precise pre-assembled system resulted in the efficient synthesis of hetero[4]rotaxane with a high-level of structural complexity under the “CuAAC” reaction. |
format | Online Article Text |
id | pubmed-5535066 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-55350662017-08-14 One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy Fu, Xin Zhang, Qi Rao, Si-Jia Qu, Da-Hui Tian, He Chem Sci Chemistry The construction and efficient synthesis of hetero[n]rotaxanes with high structural complexity are always attractive challenges. Herein, we demonstrate a facile one-pot preparation of a hetero[4]rotaxane, by employing a self-sorting strategy, which contains an interpenetrated dibenzo-24-crown-8 (DB24C8) based [c2]daisy chain structure and is ended with a benzo-21-crown-7 (B21C7) based rotaxane at each side. The key to the design involved encoding the selective threading using a steric hindrance-related “language”, where highly selective self-assemblies occurred in a three-component self-sorting process, which included the threading of a benzylalkylammonium into a B21C7 and interpenetrated dimerized formation of a DB24C8 based [c2]daisy chain simultaneously; the precise pre-assembled system resulted in the efficient synthesis of hetero[4]rotaxane with a high-level of structural complexity under the “CuAAC” reaction. Royal Society of Chemistry 2016-03-01 2016-01-12 /pmc/articles/PMC5535066/ /pubmed/28808537 http://dx.doi.org/10.1039/c5sc04844c Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Fu, Xin Zhang, Qi Rao, Si-Jia Qu, Da-Hui Tian, He One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy |
title | One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
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title_full | One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
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title_fullStr | One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
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title_full_unstemmed | One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
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title_short | One-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy
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title_sort | one-pot synthesis of a [c2]daisy-chain-containing hetero[4]rotaxane via a self-sorting strategy |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5535066/ https://www.ncbi.nlm.nih.gov/pubmed/28808537 http://dx.doi.org/10.1039/c5sc04844c |
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