Investigation of contrasting hydrogen bonding pattern of 3-(phenylamino)-cyclohexen-1-one with solvents in the ground and excited states

In this paper, we report the contrasting pattern of hydrogen bonding between solvents and 3-(phenylamino)-cyclohexen-1-one (PACO), an intramolecular charge transfer (ICT) molecule in the ground and excited states. The uniqueness of this molecule has been revealed through linear free energy relationship based Kamlet-Taft analysis which indicates that the polarizability (π∗) and the hydrogen bond acceptor abilities (β) of the solvent are mainly responsible for the observed absorption spectra of the probe while polarizability (π∗) and the hydrogen bond donor abilities (α) of the solvents mainly determine its emitting profile. This investigation helps us to decipher the ground and excited state behavior of the hydrogen bonding sites present in PACO. These findings are also expected to be useful in understanding the nature of other molecules containing multiple H-bonding sites.

Graphical abstractDownload full-size imageHighlights► H-bonding pattern of PACO with solvents has been investigated experimentally. ► Both polarity and H-bonding ability of a solvent affect the photophysics of PACO. ► The nature of multiple H-bonding sites of this molecule has been deciphered.