A Multistate Molecular Switch Based on the 6,8-Rearrangement in Bromo-apigeninidin Operated with pH and Host-Guest Inputs

Nuno Basílio; Luís Cruz; Victor De Freitas; Fernando Pina

doi:10.1021/acs.jpcb.6b03694

A Multistate Molecular Switch Based on the 6,8-Rearrangement in Bromo-apigeninidin Operated with pH and Host-Guest Inputs

Nuno Basílio, Luís Cruz, Victor De Freitas, Fernando Pina

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

The equilibrium between 6- and 8-bromo-apigeninidin is quantitatively displaced toward the formation of the former in the presence of cucurbit[7]uril because of the selective recognition of the 6-bromo isomer by the host. This phenomenon permits us to conceive a unidirectional multistate switch addressed with host-guest inputs and enables the reversible activation and deactivation of the 6-/8-bromo-apigeninidin dynamic molecular multistate through coupled host-guest and pH inputs.

Original language	English
Pages (from-to)	7053-7061
Number of pages	9
Journal	Journal of Physical Chemistry B
Volume	120
Issue number	29
DOIs	https://doi.org/10.1021/acs.jpcb.6b03694
Publication status	Published - 28 Jul 2016

Keywords

PK(A) SHIFTS
FLAVYLIUM COMPOUNDS
BETA-CYCLODEXTRIN
ANTHOCYANINS
COMPLEXES
SYSTEMS
REARRANGEMENT
NANOPARTICLES
PHOTOCHROMISM
STABILITY

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10.1021/acs.jpcb.6b03694Licence: CC BY-NC

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title = "A Multistate Molecular Switch Based on the 6,8-Rearrangement in Bromo-apigeninidin Operated with pH and Host-Guest Inputs",

abstract = "The equilibrium between 6- and 8-bromo-apigeninidin is quantitatively displaced toward the formation of the former in the presence of cucurbit[7]uril because of the selective recognition of the 6-bromo isomer by the host. This phenomenon permits us to conceive a unidirectional multistate switch addressed with host-guest inputs and enables the reversible activation and deactivation of the 6-/8-bromo-apigeninidin dynamic molecular multistate through coupled host-guest and pH inputs.",

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author = "Nuno Bas{\'i}lio and Lu{\'i}s Cruz and {De Freitas}, Victor and Fernando Pina",

note = "Sem PDF. Associated Laboratory for Sustainable Chemistry, Clean Processes and Technologies, LAQV national funds from FCT/MEC (UID/QUI/50006/2013) ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265) Fundacao para a Ciencia e a Tecnologia (RECI/BBB-BQB/0230/2012) FCT/MEC (SFRH/BPD/72652/2010; SFRH/BPD/84805/2012)",

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doi = "10.1021/acs.jpcb.6b03694",

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AU - Basílio, Nuno

AU - Cruz, Luís

AU - De Freitas, Victor

AU - Pina, Fernando

N1 - Sem PDF. Associated Laboratory for Sustainable Chemistry, Clean Processes and Technologies, LAQV national funds from FCT/MEC (UID/QUI/50006/2013) ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265) Fundacao para a Ciencia e a Tecnologia (RECI/BBB-BQB/0230/2012) FCT/MEC (SFRH/BPD/72652/2010; SFRH/BPD/84805/2012)

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N2 - The equilibrium between 6- and 8-bromo-apigeninidin is quantitatively displaced toward the formation of the former in the presence of cucurbit[7]uril because of the selective recognition of the 6-bromo isomer by the host. This phenomenon permits us to conceive a unidirectional multistate switch addressed with host-guest inputs and enables the reversible activation and deactivation of the 6-/8-bromo-apigeninidin dynamic molecular multistate through coupled host-guest and pH inputs.

AB - The equilibrium between 6- and 8-bromo-apigeninidin is quantitatively displaced toward the formation of the former in the presence of cucurbit[7]uril because of the selective recognition of the 6-bromo isomer by the host. This phenomenon permits us to conceive a unidirectional multistate switch addressed with host-guest inputs and enables the reversible activation and deactivation of the 6-/8-bromo-apigeninidin dynamic molecular multistate through coupled host-guest and pH inputs.

KW - PK(A) SHIFTS

KW - FLAVYLIUM COMPOUNDS

KW - BETA-CYCLODEXTRIN

KW - ANTHOCYANINS

KW - COMPLEXES

KW - SYSTEMS

KW - REARRANGEMENT

KW - NANOPARTICLES

KW - PHOTOCHROMISM

KW - STABILITY

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DO - 10.1021/acs.jpcb.6b03694

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SN - 1520-6106

VL - 120

SP - 7053

EP - 7061

JO - Journal of Physical Chemistry B

JF - Journal of Physical Chemistry B

IS - 29

ER -

A Multistate Molecular Switch Based on the 6,8-Rearrangement in Bromo-apigeninidin Operated with pH and Host-Guest Inputs

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Keywords

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