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Achieving Complexity at the Bottom: Molecular Metamorphosis Generated by Anthocyanins and Related Compounds
[Image: see text] The concept of molecular metamorphosis is described. A molecule (flavylium cation) generates a sequence of other different molecules by means of external stimuli. The reversibility of the system allows for the flavylium cation to be recovered by other external stimuli, completing o...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600532/ https://www.ncbi.nlm.nih.gov/pubmed/34805653 http://dx.doi.org/10.1021/acsomega.1c04456 |
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author | Basílio, Nuno Parola, A. Jorge Sousa, Diogo Petrov, Vesselin Cruz, Luis de Freitas, Victor Pina, Fernando |
author_facet | Basílio, Nuno Parola, A. Jorge Sousa, Diogo Petrov, Vesselin Cruz, Luis de Freitas, Victor Pina, Fernando |
author_sort | Basílio, Nuno |
collection | PubMed |
description | [Image: see text] The concept of molecular metamorphosis is described. A molecule (flavylium cation) generates a sequence of other different molecules by means of external stimuli. The reversibility of the system allows for the flavylium cation to be recovered by other external stimuli, completing one cycle. Differently from supramolecular chemistry, molecular metamorphosis is not a bottom-up approach. All events occur at the bottom. The procedures to characterize the kinetics and thermodynamics of the cycles are summarized. They are based on direct pH jumps (addition of a base to the flavylium cation) and reverse pH jumps (addition of an acid to equilibrated solutions at higher pH values). Stopped flow is an indispensable tool to characterize these systems. The following metamorphic cycles will be described to illustrate the concept: (i) introducing the flavanone in the metamorphic system and illustrating the concept of a timer at the molecular level; (ii) response of the flavylium-based metamorphosis to light inputs and the write-lock-read-unlock-erase molecular system; (iii) a one-way cycle of direct–reverse pH jumps; (iv) interconversion of the flavylium cation with 2,2′-spirobis[chromene] derivatives; (v) 6,8 A-ring substituent rearrangements. |
format | Online Article Text |
id | pubmed-8600532 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-86005322021-11-19 Achieving Complexity at the Bottom: Molecular Metamorphosis Generated by Anthocyanins and Related Compounds Basílio, Nuno Parola, A. Jorge Sousa, Diogo Petrov, Vesselin Cruz, Luis de Freitas, Victor Pina, Fernando ACS Omega [Image: see text] The concept of molecular metamorphosis is described. A molecule (flavylium cation) generates a sequence of other different molecules by means of external stimuli. The reversibility of the system allows for the flavylium cation to be recovered by other external stimuli, completing one cycle. Differently from supramolecular chemistry, molecular metamorphosis is not a bottom-up approach. All events occur at the bottom. The procedures to characterize the kinetics and thermodynamics of the cycles are summarized. They are based on direct pH jumps (addition of a base to the flavylium cation) and reverse pH jumps (addition of an acid to equilibrated solutions at higher pH values). Stopped flow is an indispensable tool to characterize these systems. The following metamorphic cycles will be described to illustrate the concept: (i) introducing the flavanone in the metamorphic system and illustrating the concept of a timer at the molecular level; (ii) response of the flavylium-based metamorphosis to light inputs and the write-lock-read-unlock-erase molecular system; (iii) a one-way cycle of direct–reverse pH jumps; (iv) interconversion of the flavylium cation with 2,2′-spirobis[chromene] derivatives; (v) 6,8 A-ring substituent rearrangements. American Chemical Society 2021-10-13 /pmc/articles/PMC8600532/ /pubmed/34805653 http://dx.doi.org/10.1021/acsomega.1c04456 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Basílio, Nuno Parola, A. Jorge Sousa, Diogo Petrov, Vesselin Cruz, Luis de Freitas, Victor Pina, Fernando Achieving Complexity at the Bottom: Molecular Metamorphosis Generated by Anthocyanins and Related Compounds |
title | Achieving Complexity at the Bottom: Molecular Metamorphosis
Generated by Anthocyanins and Related Compounds |
title_full | Achieving Complexity at the Bottom: Molecular Metamorphosis
Generated by Anthocyanins and Related Compounds |
title_fullStr | Achieving Complexity at the Bottom: Molecular Metamorphosis
Generated by Anthocyanins and Related Compounds |
title_full_unstemmed | Achieving Complexity at the Bottom: Molecular Metamorphosis
Generated by Anthocyanins and Related Compounds |
title_short | Achieving Complexity at the Bottom: Molecular Metamorphosis
Generated by Anthocyanins and Related Compounds |
title_sort | achieving complexity at the bottom: molecular metamorphosis
generated by anthocyanins and related compounds |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600532/ https://www.ncbi.nlm.nih.gov/pubmed/34805653 http://dx.doi.org/10.1021/acsomega.1c04456 |
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