Fluorescence enhancement of bis(2,4,6-trihydroxyphenyl)squaraine anion by 2 : 1 host–guest complexation with β-cyclodextrin
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Faraday Transactions
- Vol. 88 (23) , 3419-3422
- https://doi.org/10.1039/ft9928803419
Abstract
β-Cyclodextrin (β-CD) forms a 2: 1 inclusion complex with the anion of bis(2,4,6-trihydroxyphenyl)squaraine dye (Sq), in aqueous solutions, bringing about a significant enhancement in the fluorescence yield (ca. 90-fold) and the stability of the dye anion. Apart from the effect of the hydrophobic environment and the decrease in rotational freedom brought about by β-CD encapsulation, intramolecular hydrogen bonding between the OH groups on the phenyl rings and the oxygen atoms in the central cyclobutane ring in the anion guest molecule can significantly contribute to the stiffening of the molecule in the excited state. In the absence of β-CD, intermolecular hydrogen bonding with solvent molecules disrupts the intramolecular hydrogen-bonding processes, bringing about a decrease in the fluorescence yield of the anion.Keywords
This publication has 15 references indexed in Scilit:
- A modified cyclodextrin as a guest responsive colour-change indicatorNature, 1992
- Porphyrins-cyclodextrin. 1. Photooxidation of zinc tetrakis(4-sulfonatophenyl)porphyrin (ZnTSPP) in cyclodextrin cavities: the characterization of ZnTSPP dication. Photolysis, radiolysis, and NMR studiesThe Journal of Physical Chemistry, 1991
- Fluorescence of 1-naphthol induced by 2 : 1 complexation with N(N′-formyl-L-phenylalanyl)-β-cyclodextrinJournal of the Chemical Society, Chemical Communications, 1991
- Phosphorescent PET (photoinduced electron transfer) sensors: prototypical examples for proton monitoring and a ‘message in a bottle’ enhancement strategy with cyclodextrinsJournal of the Chemical Society, Chemical Communications, 1991
- Cyclodextrin TechnologyPublished by Springer Nature ,1988
- Inclusional association of a fluorescence detergent probe with cyclodextrins. Microscopic environment of the interior of a cyclodextrin cavityJournal of the American Chemical Society, 1982
- Absolute luminescence yield of cresyl violet. A standard for the redThe Journal of Physical Chemistry, 1979
- Specific inclusion catalysis by .beta.-cyclodextrin in the one-step preparation of vitamin K1 or K2 analogsJournal of the American Chemical Society, 1979
- Inclusion Compounds. XIX.1a The Formation of Inclusion Compounds of α-Cyclodextrin in Aqueous Solutions. Thermodynamics and KineticsJournal of the American Chemical Society, 1967
- Cyclotrimethine Dyes Derived from Squaric AcidAngewandte Chemie International Edition in English, 1965