Inclusion Complexes of a Metastable‐State Photoacid with High Acidity and Chemical Stability (in EN)
Abstract Metastable‐state merocyanine photoacids (MCHs) have been widely applied to various chemical, material and biomedical areas to drive or control chemical processes with light. In this work, stoichiometry and association constants have been determined for inclusion complexes of a photoacid MCH1 ((E)‐3‐(2‐(2‐hydroxystyryl)‐3,3‐dimethyl‐3H‐indol‐1‐ium‐1‐yl)propane‐1‐sulfonate) withβ‐cyclodextrin (β‐CD), 2‐hydroxypropyl‐β‐CD (HP‐β‐CD),γ‐CD and HP‐γ‐CD by means of UV‐Vis absorption spectroscopic titrations. The inclusion complexes were studied to enhance acidity and chemical stability. Kinetic study showed that CDs stabilized the acidic metastable state and slowed its thermal relaxation. The acidity of the ground and metastable state (pKaGSand pKaMS) increased upon addition of CDs. The pKaMSof [MCH1 ⋅ (γ‐CD)2] is as low as 0.92 in comparison with 2.24 for MCH1, which is close to the lowest pKaMSvalues (1.20 and 1.03) reported previously, in which case the MCH1 was structurally modified with alkylammonium side chains. Addition of CDs also significantly enhanced the chemical stability of MCH1 against hydrolysis, which is one of the major concerns for the application of MCHs. In particular, the addition of HP‐β‐CD increased the half‐life of MCH1 in aqueous solution more than four‐fold. Moreover, the quantum chemical calculations confirmed the stoichiometry and analyzed the binding sites and hydrogen bonds of the inclusion complexes.
- Research Organization:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Organization:
- USDOE
- Grant/Contract Number:
- AC05-00OR22725
- OSTI ID:
- 2580606
- Journal Information:
- ChemPhotoChem, Journal Name: ChemPhotoChem Journal Issue: 12 Vol. 7; ISSN 2367-0932
- Publisher:
- Wiley - European Chemical Societies PublishingCopyright Statement
- Country of Publication:
- United States
- Language:
- EN
Similar Records
Comparing the extraction performance of cyclodextrin-containing supramolecular deep eutectic solvents versus conventional deep eutectic solvents by headspace single drop microextraction
Removal of aromatic hydrocarbon compounds by hydroxypropyl-cyclodextrin