A combined experimental and theoretical study on p‐sulfonatocalix[4]arene encapsulated 7‐methoxycoumarin

A combined experimental and theoretical study on p‐sulfonatocalix[4]arene encapsulated... Host‐guest interactions are essential in chemistry, biology, medicine and environmental science. In this combined experimental and theoretical contribution, the encapsulation of 7‐methoxycoumarin (herniarin, 7MC) with p‐sulfonatocalix[4]arene (p‐SC4) is studied using absorption and fluorescence spectroscopy, cyclic voltammetry and computational approaches. The 1:1 stoichiometry is confirmed using Job's plot. Our results show that the keto group of 7MC is the main source for electrochemical conversion of this complex. The excited state 7MC radiative decay is studied using time‐correlated single photon counting technique. The computed UV‐Vis absorption spectra for this complex at gas phase and solvent are online with the experimental spectra. Moreover, we determined the binding energy and the binding constant of the 7MC‐p‐SC4 complex. Density functional theory computations revealed that stabilization of the complex formed by p‐SC4 and 7MC is due to weak noncovalent and dispersive types of interactions. A comparison with encapsulation of amino acids by p‐SC4 is also conducted. Finally, we show that the flexibility of p‐SC4 and the weak nature of its interaction with 7MC are on the origin of the reversibility of encapsulation, which is mandatory for applications such as drug delivery. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Physical Organic Chemistry Wiley

A combined experimental and theoretical study on p‐sulfonatocalix[4]arene encapsulated 7‐methoxycoumarin

Loading next page...
 
/lp/wiley/a-combined-experimental-and-theoretical-study-on-p-sulfonatocalix-4-BodPCtkshD
Publisher
Wiley
Copyright
Copyright © 2018 John Wiley & Sons, Ltd.
ISSN
0894-3230
eISSN
1099-1395
D.O.I.
10.1002/poc.3788
Publisher site
See Article on Publisher Site

Abstract

Host‐guest interactions are essential in chemistry, biology, medicine and environmental science. In this combined experimental and theoretical contribution, the encapsulation of 7‐methoxycoumarin (herniarin, 7MC) with p‐sulfonatocalix[4]arene (p‐SC4) is studied using absorption and fluorescence spectroscopy, cyclic voltammetry and computational approaches. The 1:1 stoichiometry is confirmed using Job's plot. Our results show that the keto group of 7MC is the main source for electrochemical conversion of this complex. The excited state 7MC radiative decay is studied using time‐correlated single photon counting technique. The computed UV‐Vis absorption spectra for this complex at gas phase and solvent are online with the experimental spectra. Moreover, we determined the binding energy and the binding constant of the 7MC‐p‐SC4 complex. Density functional theory computations revealed that stabilization of the complex formed by p‐SC4 and 7MC is due to weak noncovalent and dispersive types of interactions. A comparison with encapsulation of amino acids by p‐SC4 is also conducted. Finally, we show that the flexibility of p‐SC4 and the weak nature of its interaction with 7MC are on the origin of the reversibility of encapsulation, which is mandatory for applications such as drug delivery.

Journal

Journal of Physical Organic ChemistryWiley

Published: Jan 1, 2018

Keywords: ; ; ; ;

References

You’re reading a free preview. Subscribe to read the entire article.


DeepDyve is your
personal research library

It’s your single place to instantly
discover and read the research
that matters to you.

Enjoy affordable access to
over 18 million articles from more than
15,000 peer-reviewed journals.

All for just $49/month

Explore the DeepDyve Library

Search

Query the DeepDyve database, plus search all of PubMed and Google Scholar seamlessly

Organize

Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place.

Access

Get unlimited, online access to over 18 million full-text articles from more than 15,000 scientific journals.

Your journals are on DeepDyve

Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.

All the latest content is available, no embargo periods.

See the journals in your area

DeepDyve

Freelancer

DeepDyve

Pro

Price

FREE

$49/month
$360/year

Save searches from
Google Scholar,
PubMed

Create lists to
organize your research

Export lists, citations

Read DeepDyve articles

Abstract access only

Unlimited access to over
18 million full-text articles

Print

20 pages / month

PDF Discount

20% off