Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 30, Pages 9257-9263Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902968
Keywords
sensors; bond twisting; fluorescence; thioflavin T; time-resolved spectroscopy
Categories
Funding
- Radiation & Photochemistry Division
- Indian Science Academies (IASC, INSA NASI)
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An ultrafast intramolecular bond twisting process is known to be the responsible mechanism for the sensing activity of the extensively used amyloid fibril sensor thioflavin T (ThT). However, it is not yet known which one of the two possible single bonds in ThT is actually involved in the twisting process. To resolve this fundamental issue, two derivatives of ThT have been designed and synthesized and subsequently their photophysical properties have been studied in different solvents. It is understood from the present study that the rotation around the central C C single bond, and not that around the C-N single bond, is primarily responsible for the sensor activity of ThT. Detailed viscosity-dependent fluorescence studies revealed that the ThT derivative with restricted C-N bond rotation acts as a better sensor than the derivative with free C-N bond rotation. The better sensory activity is directly correlated with a shorter excited-state lifetime. Results obtained from the photophysical studies of the TIT derivatives have also been supported by the results obtained from quantum chemical calculations.
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