@article{ff8acb0eb3a7419988fca14ea0a73d4a,
title = "2-Hydroxychalcone-β-Cyclodextrin Conjugate with pH-Modulated Photoresponsive Binding Properties",
abstract = "Stimuli-responsive supramolecular receptors are important building blocks for the construction of self-assembled functional materials. We report the design and synthesis of a pH- and light-responsive 2-hydroxychalcone-β-cyclodextrin conjugate (1-Ct) and its characterization by spectroscopic and computational methods. 1-Ct follows the typical reaction network of trans-chalcone-flavylium photoswitches. Upon light irradiation, 1-Ct can be photochemically converted into the cis-chalcone/hemiketal forms (1-Cc/1-B) under neutral pH conditions or to the flavylium cation (1-AH+) at acidic pH values. This stimuli-responsive β-cyclodextrin host, 1-Ct, was found to form stronger intramolecular self-inclusion complexes (Kintra= 14) than 1-AH+(Kintra= 3) and weaker than 1-Cc/1-B (overall Kintra= 179), allowing control over their stability and binding properties by combinations of pH and light stimuli.",
keywords = "Binding energy, Functional materials, pH, Binding properties, Building blockes, Chalcones, Flavylium, Hemiketals, Light irradiations, Photo-responsive, Photoswitch, Reaction network, Stimuli-responsive, Cyclodextrins",
author = "Micael Paulino and Ignacio P{\'e}rez-Juste and Cid, {Mar{\'i}a Magdalena} and {Da Silva}, {Jos{\'e} P.} and Pereira, {M. Manuela A.} and Nuno Bas{\'i}lio",
note = "info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT# info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT# info:eu-repo/grantAgreement/FCT/9444 - RNIIIE/PINFRA%2F22161%2F2016/PT# info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04326%2F2020/PT# info:eu-repo/grantAgreement/FCT/9471 - RIDTI/PTDC%2FQUI-COL%2F32351%2F2017/PT# info:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00466%2F2017%2FCP1462%2FCT0013/PT# Funding Information: FCT/MCTES is also acknowledged for supporting the National Portuguese NMR Network (ROTEIRO/0031/2013, cofinanced by FEDER through COMPETE 2020, POCI, PORL, and FCT through PIDDAC). This study also received Portuguese national funds from the operational programs CRESC Algarve 2020 and COMPETE 2020 through project EMBRC.PT ALG-01-0145-FEDER-022121. Publisher Copyright: {\textcopyright} 2022 Authors. All rights reserved.",
year = "2022",
month = nov,
day = "4",
doi = "10.1021/acs.joc.2c01875",
language = "English",
volume = "87",
pages = "14422--14432",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "ACS - American Chemical Society",
number = "21",
}