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Prediction of the most preferable rotamer of meta-aminophenol in β-cyclodextrin cavity in aqueous medium by using spectroscopic and DFT computational studies


Meta-aminophenol (m-AP) was used as a guest molecule to be incorporated into the hydrophobic nano-cavity of the host molecule β-cyclodextrin (β-CD) to form host–guest inclusion complex in aqueous medium. For this, we employed spectrometric titration method, i.e., β-CD was added gradually in an aqueous solution of m-AP maintaining a fixed concentration of m-AP. We investigated the changes in the photophysical properties of m-AP through inclusion complex formation in β-CD in aqueous medium by using steady state and time-resolved spectroscopic techniques as well as density functional theory (DFT) computations. Benesi–Hildebrand method was used to find the stoichiometry and association constant at two concentration ranges of β-CD. The average fluorescence lifetime of m-AP was found to increase from 0.17 ns in absence of β-CD to 3.69 ns in presence of β-CD (highest concentration used). DFT computations carried out in water medium clearly indicate that the inclusion complex is more stable for the cis-rotameric conformation of m-AP rather than trans.

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SS thanks Prof. Samita Basu (Chemical Sciences Division, Saha Institute of Nuclear Physics, Kolkata—700 064, India) for her valuable scientific suggestions and Mr. Ajay Das (Chemical Sciences Division, Saha Institute of Nuclear Physics, Kolkata—700 064, India) for fluorescence lifetime measurements. Also, SS sincerely acknowledges Prof. Pranab Sarkar, Dr. Md. Motin Seikh (Department of Chemistry, Siksha Bhavana, Visva-Bharati, Santiniketan—731 235, India) and Dr. Nilanjan Bondyopadhaya (ISERC, Siksha Bhavana, Visva-Bharati, Santiniketan—731 235, India) for helping in DFT calculations.

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Correspondence to Subrata Sinha.

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Majhi, K., Bandyopadhyay, P., Khatun, R. et al. Prediction of the most preferable rotamer of meta-aminophenol in β-cyclodextrin cavity in aqueous medium by using spectroscopic and DFT computational studies. J Incl Phenom Macrocycl Chem (2020).

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  • m-Aminophenol
  • β-Cyclodextrin
  • Benesi–Hildebrand plot
  • NBO analysis