Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies | European Journal of Chemistry

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Published: Mar 31, 2023

DOI: https://doi.org/10.5155/eurjchem.14.1.16-29.2320

Keywords:

Phenothiazine, Quantum yield, Optical band gap, Solvatochromism, Cyclic voltammetry, Photophysical property

Section

Research Article

Issue

Vol. 14 No. 1 (2023): March 2023

Dates

Received 2022-08-12
Accepted 2022-11-30
Published 2023-03-31

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Shivaraj Mantur

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0003-4066-0663

Mallikarjun Kalagouda Patil

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Laser Spectroscopy Program, Department of Physics, Karnatak University, Dharwad, 580003, India

https://orcid.org/0000-0001-7126-9486

Afra Quasar Abdul Rasheed Nadaf

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0002-0962-5547

Mahesh Sadashivappa Najare

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0002-4649-9439

Mohammed Yaseen

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0003-1148-4090

Aravind Raviraj Nesaragi

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0002-0384-655X

Sanjeev Ramchandra Inamdar

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Laser Spectroscopy Program, Department of Physics, Karnatak University, Dharwad, 580003, India

https://orcid.org/0000-0003-3398-4897

Imtiyaz Ahmed Khazi

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

https://orcid.org/0000-0001-8216-1913

Ravindra Ramappa Kamble

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Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India

http://orcid.org/0000-0002-0384-655X

Abstract

A new class of probes was synthesized using a simple and efficient synthetic protocol. These compounds (PTZ-6(a-e)) have the phenothiazine (PTZ) moiety as the electron donor (D) and substituted aldehydes along with the acrylonitrile group, which acts as the electron acceptor (A), thus making D-π-A push-pull system. The structures of the newly synthesized series of small organic target molecules PTZ-6(a-e) were investigated and confirmed by spectros-copic techniques. The optical/solvatochromic properties were studied in detail by UV-vis absorption and fluorescence spectroscopy, because the molecules have shown good solubility in organic solvents. The density functional theory (DFT) model with the CAM-B3LYP function is utilized to study the photophysical properties of the probes, as these probes exhibited orange-to-red emission. Optical band gap values ranged from 2.32 to 2.50 eV, and these probes exhibited good thermal stability with a melting temperature of 136 to 198 °C and a T_5d temperature range from 335 to 354 °C. The cyclic voltammetry study confirms that the E_ox^onset values of the target compounds are 0.80 eV. The quantum yields (Φ) of the probes are measured experimentally in ethanol and the Stokes shifts are observed to be in the range of 4846-9430 cm^-1. The results displayed that novel (D-A-D) chromophores could play an important role in organic optoelectronics.

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Mantur, S.; Patil, M. K.; Nadaf, A. Q. A. R.; Najare, M. S.; Yaseen, M.; Nesaragi, A. R.; Inamdar, S. R.; Khazi, I. A.; Kamble, R. R. Orange to Red Emissive Aldehyde Substituted Donor-π-Acceptor Phenothiazine Derivatives: Optoelectronic, DFT and Thermal Studies. Eur. J. Chem. 2023, 14, 16-29.

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Supporting Agencies

The University Grants Commission, New Delhi, India, for providing necessary facilities under UGC-SRF (Sr. No.2121510180 Ref. No. December 20, 2015) and Department of Science and Technology for providing the Inspire Fellowship.

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