Role of solvent H-bonding and polarity on photophysical properties of a benzothiazole-based ratiometric amyloid fibril sensor
| Autor: | Subrata Chattopadhyay, Aruna K. Mora, Sushant Murudkar, Alagarsamy Alamelu, Sukhendu Nath |
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| Rok vydání: | 2019 |
| Předmět: |
Hydrogen bond
General Chemical Engineering Solvatochromism General Physics and Astronomy 02 engineering and technology General Chemistry Dihedral angle 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry 01 natural sciences 0104 chemical sciences Solvent chemistry.chemical_compound Aniline chemistry Benzothiazole Molecule Steady state (chemistry) 0210 nano-technology |
| Zdroj: | Journal of Photochemistry and Photobiology A: Chemistry. 373:20-27 |
| ISSN: | 1010-6030 |
| DOI: | 10.1016/j.jphotochem.2018.12.030 |
| Popis: | Detailed photophysical properties of 2-[2′-Me,4′-(dimethylamino)-phenyl]benzothiazole (2Me-DABT), a potential ratiometric amyloid fibril sensor, have been investigated in different solvents and solvent mixtures using steady state and time-resolved spectroscopic techniques. Our studies show that emission properties of 2Me-DABT are significantly modulated by polarity of solvent media. Extent of solvatochromism (3585 cm−1) shown by 2Me-DABT is quite large and can be used to monitor micropolarity of different complex media. Further, Stokes’ shift (>10,000 cm−1) shown by 2Me-DABT in all studied solvents is also much larger than most common molecular probes. It has also been shown that hydrogen bonding with solvent molecules results in large modulation in photophysical properties of 2Me-DABT. The H-bonding with water molecules induces a large change (39°) in the dihedral angle between benzothiazole and aniline moieties resulting large changes in photophysical properties of 2Me-DABT in polar protic solvents. Photophysical properties reported herein are used to explain observed amyloid sensing behaviour of 2Me-DABT. Detailed quantum chemical calculations are performed to support the experimental results. |
| Databáze: | OpenAIRE |
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