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Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox
Oxanorbornene-fused double-stranded macrocycles, represented by kohnkene, are not only synthetic precursors toward short segments of zigzag carbon nanotubes but also typical cavitands processing an intrinsic cavity. However, their capability to bind guest molecules in solution remained unexplored. H...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8864699/ https://www.ncbi.nlm.nih.gov/pubmed/35310504 http://dx.doi.org/10.1039/d1sc06553j |
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author | Chen, Han Xia, Zeming Miao, Qian |
author_facet | Chen, Han Xia, Zeming Miao, Qian |
author_sort | Chen, Han |
collection | PubMed |
description | Oxanorbornene-fused double-stranded macrocycles, represented by kohnkene, are not only synthetic precursors toward short segments of zigzag carbon nanotubes but also typical cavitands processing an intrinsic cavity. However, their capability to bind guest molecules in solution remained unexplored. Herein we report a new member of oxanorbornene-fused double-stranded macrocycles, which is named a nanobox herein because of its shape. Reductive aromatization of this oxanorbornene-fused nanobox leads to observation of a new zigzag carbon nanobelt by high resolution mass spectroscopy. The fluorescence titration and NMR experiments indicate that this nanobox encapsulates C(70) in solution with a binding constant of (3.2 ± 0.1) × 10(6) M(−1) in toluene and a high selectivity against C(60) and its derivatives. As found from the X-ray crystallographic analysis, this nanobox changes the shape of its cross-section from a rhombus to nearly a square upon accommodating C(60). |
format | Online Article Text |
id | pubmed-8864699 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-88646992022-03-17 Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox Chen, Han Xia, Zeming Miao, Qian Chem Sci Chemistry Oxanorbornene-fused double-stranded macrocycles, represented by kohnkene, are not only synthetic precursors toward short segments of zigzag carbon nanotubes but also typical cavitands processing an intrinsic cavity. However, their capability to bind guest molecules in solution remained unexplored. Herein we report a new member of oxanorbornene-fused double-stranded macrocycles, which is named a nanobox herein because of its shape. Reductive aromatization of this oxanorbornene-fused nanobox leads to observation of a new zigzag carbon nanobelt by high resolution mass spectroscopy. The fluorescence titration and NMR experiments indicate that this nanobox encapsulates C(70) in solution with a binding constant of (3.2 ± 0.1) × 10(6) M(−1) in toluene and a high selectivity against C(60) and its derivatives. As found from the X-ray crystallographic analysis, this nanobox changes the shape of its cross-section from a rhombus to nearly a square upon accommodating C(60). The Royal Society of Chemistry 2022-01-13 /pmc/articles/PMC8864699/ /pubmed/35310504 http://dx.doi.org/10.1039/d1sc06553j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Chen, Han Xia, Zeming Miao, Qian Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title | Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title_full | Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title_fullStr | Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title_full_unstemmed | Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title_short | Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
title_sort | synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8864699/ https://www.ncbi.nlm.nih.gov/pubmed/35310504 http://dx.doi.org/10.1039/d1sc06553j |
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