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334851

Solvatochromic A-D-A bithiophene derivative, steady state and time resolved studies and DFT calculations.

Article

Last updated: 01 Jan 2025

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Abstract

Steady state and time resolved properties of 5-(5-(4-fluorophenyl)thiophen-2-yl)thiophene-2-carboxamidine (FTTA) in a variety of solvents are reported. FTTA presents system of the type A-D-A (acceptor--bridge-donor-acceptor) where the bithiophene bridge acts as electron donor and the 4-fluorophenyl and amidine groups at both terminals act as electron acceptors. Solvent effect on the absorption spectra shows a slight solvent polarity dependence that covers a narrow range from 368 nm in cyclohexane to 379 in acetonitrile. On the other hand, change of the fluorescence emission maximum in aprotic solvents was only about 40 nm from acetonitrile to cyclohexane. The larger variation of the fluorescence emission maximum with the polarity of the solvent gives a conjecture that the nature of emission of from a state with intramolecular charge transfer character. However, the small dependence of the absorption maximum on the solvent polarity is attributed to a smaller dipole moment of the ground state than that of the excited state. Density functional theory (DFT) calculations shows a planar geometry in the excited state and non-planar geometry in the ground state. Dipole moments obtained from DFT and TD-DFT (Time-dependent density-functional theory) are also reported. Fluorescence lifetime, , and fluorescence quantum yield, f, were found to decrease with the emission energy, while the emission energy decreases as the solvent polarity increases. To ascertain the contributions of specific and non-specific solute-solvent interactions, we have utilized multi-parametric relationships as developed by Kamlet-Taft, Catalán, and Laurence. In every instance, it was discovered that non-specific interactions were largely dominating.

DOI

10.21608/ejchem.2024.245680.8800

Keywords

fluorosolvatochromism, Intramolecular charge transfer, Fluorescence, DFT

Authors

First Name

Ahmed

Last Name

Soliman

MiddleName

-

Affiliation

Department of chemistry, Faculty of Science, Alazhar University,

Email

ahmed.soliman001@gmail.com

City

-

Orcid

-

First Name

Mohamed

Last Name

Ismail

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science, Mansura University

Email

ismail_158@yahoo.com

City

-

Orcid

-

First Name

Badr

Last Name

Elsayed

MiddleName

Awad

Affiliation

Chemistry Department, Faculty of Science, Al-Azhar University, Cairo, Egyp

Email

badrelsayed@gmail.com

City

Nasr City

Orcid

0000000318853266

First Name

Ahmed

Last Name

Mora

MiddleName

-

Affiliation

Department of chemistry, Faculty of Science, Alazhar University

Email

amedtalaatmora@gmail.com

City

-

Orcid

-

First Name

Ayman

Last Name

Abdel-Shafi

MiddleName

A

Affiliation

Alkhalifa Almamoun

Email

aaashafi@sci.asu.edu.eg

City

Cairo

Orcid

0000-0002-3426-6486

Volume

67

Article Issue

7

Related Issue

47288

Issue Date

2024-07-01

Receive Date

2023-10-30

Publish Date

2024-07-01

Page Start

171

Page End

182

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_334851.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=334851

Order

334,851

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Solvatochromic A-D-A bithiophene derivative, steady state and time resolved studies and DFT calculations.

Details

Type

Article

Created At

30 Dec 2024