Solubilization of Pyridone-Based Fluorescent Tag by
Complexation in Cucurbit[7]uril
Posted on 2019-01-10 - 19:36
Aimed
at further exploring the hosting properties of cucurbit[7]uril
(CB7), we have exploited the spectroscopic and photophysical properties
of a known fluorescent label as the guest molecule, namely, 3-cyano-6-(2-thienyl)-4-trifluoromethyl
pyridine (TFP), in neat solvents. The formation of an inclusion host–guest
complex with CB7 was checked by UV–vis absorption spectroscopy,
and the value of binding constant (9.7 × 105 M–1) was extracted from the spectrophotometric data.
The modulation of keto–enol equilibrium in TFP by the local
environment is governed by the interplay between dimerization through
intermolecular hydrogen bonding between individual solute molecules,
favoring the enol form, and intermolecular hydrogen bonding between
TFP and the surrounding solvents, favoring the keto form. Time-resolved
fluorescence results established that the macromolecular CB7 host
stabilizes preferentially the neutral enol form over the keto form
of TFP. Unprecedentedly, our results reveal a linear dependence of
the amplitudes of the extracted decay-associated spectra from the
time-resolved fluorescence spectra of TFP on the sum of polarity/polarizability
and hydrogen bonding parameters of the local environment, confirming
that TFP at micromolar concentration in the CB7 complexes is experiencing
a methanol-like environment. The results rationalized the 42-fold
enhancement in the solubility of TFP in water media by complexation
in CB7.
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Alzard, Reem H.; Bufaroosha, Muna S.; Al-Shamsi, Noura; Sohail, Amir; Al-Dubaili, Naji; Salem, Alaa A.; et al. (2019). Solubilization of Pyridone-Based Fluorescent Tag by
Complexation in Cucurbit[7]uril. ACS Publications. Collection. https://doi.org/10.1021/acsomega.8b02761
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AUTHORS (8)
RA
Reem H. Alzard
MB
Muna S. Bufaroosha
NA
Noura Al-Shamsi
AS
Amir Sohail
NA
Naji Al-Dubaili
AS
Alaa A. Salem
IA
Ibrahim M. Abdou
NS
Na’il Saleh