Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 17, Pages 10852-10859Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01420
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Funding
- Associate Laboratory for Green Chemistry -LAQV - FCT/MCTES [UID/QUI/50006/2019]
- FCT/MCTES [RECI/BBB-BQB/0230/2012, PTDC/QUI-COL/32351/2017, CEECIND/00466/2017]
- Spanish Ministerio de Ciencia, Innovacion y Universidades [CTQ2017-89832-P, CTQ2017-84354-P]
- Junta de Andalucia [P12-FQM-2140]
- Xunta de Galicia [GR 2007/085, IN607C 2016/03]
- European Regional Development Fund (ERDF)
- Xunta de Galicia (Centro Singular de Investigacion de Galicia accreditation 2016-2019) [ED431G/09]
- Fundação para a Ciência e a Tecnologia [PTDC/QUI-COL/32351/2017] Funding Source: FCT
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The formation of host-guest complexes between seven flavylium cations and water-soluble p-sulfonatocalix[4]arene (SC4) was investigated by UV/vis absorption, fluorescence, and NMR spectroscopies. The results show the cationic guests form complexes with affinities in the submillimolar range. A representative chalcone/flavylium photoswitch was investigated in more detail regarding its pH- and light-triggered interconversion between the two forms. The dramatic affinity differentiation of the SC4 binding of the two switchable species (40 M(-1 )for the trans- chalcone versus 3.5 X 10(4) M-1 for the flavylium cation) enables the pH-gated photocontrol of the complexation process. These responsive properties were explored to demonstrate the competitive and selective release of biologically relevant guests from their supramolecular complexes with p-sulfonatocalix[4]arene (SC4), following the principle of AND logic. The guest release can be reverted by the thermally activated reaction of the flavylium ion back to the trans-chalcone.
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