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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...

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Autores principales: Basílio, Nuno, Parola, A. Jorge, Sousa, Diogo, Petrov, Vesselin, Cruz, Luis, de Freitas, Victor, Pina, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
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.
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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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