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Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons
Developing effective strategies to improve the hydrophilicity or aqueous solubility of hydrophobic molecular scaffolds is meaningful for both academic research and industrial applications. Herein, we demonstrate that stepwise and precise N/O heteroatoms doping on a polycyclic aromatic skeleton can g...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814590/ https://www.ncbi.nlm.nih.gov/pubmed/36697950 http://dx.doi.org/10.1038/s42004-022-00724-1 |
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author | Li, Kang Hu, Jia-Min Qin, Wei-Min Guo, Jing Cai, Yue-Peng |
author_facet | Li, Kang Hu, Jia-Min Qin, Wei-Min Guo, Jing Cai, Yue-Peng |
author_sort | Li, Kang |
collection | PubMed |
description | Developing effective strategies to improve the hydrophilicity or aqueous solubility of hydrophobic molecular scaffolds is meaningful for both academic research and industrial applications. Herein, we demonstrate that stepwise and precise N/O heteroatoms doping on a polycyclic aromatic skeleton can gradually alter these structures from hydrophobic to hydrophilic, even resulting in excellent aqueous solubility. The Hansen solubility parameters (HSP) method shows that the three partial solubility parameters are closely related to N/O doping species, numbers and positions on the molecular panel. The hydrogen bonding solubility parameter indicates that the hydrogen bonding interactions between N/O doped molecules and water play a key role in enhancing hydrophilicity. Moreover, three optimized water-soluble molecules underwent a self-assembly process to form stable nanoparticles in water, thus facilitating better hydrogen bonding interactions disclosed by HSP calculations, NMR and single crystal X-ray analysis. These ensembles even show quasi-solid properties in water from NMR and luminescence perspectives. |
format | Online Article Text |
id | pubmed-9814590 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-98145902023-01-10 Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons Li, Kang Hu, Jia-Min Qin, Wei-Min Guo, Jing Cai, Yue-Peng Commun Chem Article Developing effective strategies to improve the hydrophilicity or aqueous solubility of hydrophobic molecular scaffolds is meaningful for both academic research and industrial applications. Herein, we demonstrate that stepwise and precise N/O heteroatoms doping on a polycyclic aromatic skeleton can gradually alter these structures from hydrophobic to hydrophilic, even resulting in excellent aqueous solubility. The Hansen solubility parameters (HSP) method shows that the three partial solubility parameters are closely related to N/O doping species, numbers and positions on the molecular panel. The hydrogen bonding solubility parameter indicates that the hydrogen bonding interactions between N/O doped molecules and water play a key role in enhancing hydrophilicity. Moreover, three optimized water-soluble molecules underwent a self-assembly process to form stable nanoparticles in water, thus facilitating better hydrogen bonding interactions disclosed by HSP calculations, NMR and single crystal X-ray analysis. These ensembles even show quasi-solid properties in water from NMR and luminescence perspectives. Nature Publishing Group UK 2022-08-29 /pmc/articles/PMC9814590/ /pubmed/36697950 http://dx.doi.org/10.1038/s42004-022-00724-1 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) . |
spellingShingle | Article Li, Kang Hu, Jia-Min Qin, Wei-Min Guo, Jing Cai, Yue-Peng Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title | Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title_full | Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title_fullStr | Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title_full_unstemmed | Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title_short | Precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
title_sort | precise heteroatom doping determines aqueous solubility and self-assembly behaviors for polycyclic aromatic skeletons |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9814590/ https://www.ncbi.nlm.nih.gov/pubmed/36697950 http://dx.doi.org/10.1038/s42004-022-00724-1 |
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