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Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies

Shivaraj Mantur (1) orcid , Mallikarjun Kalagouda Patil (2) orcid , Afra Quasar Abdul Rasheed Nadaf (3) orcid , Mahesh Sadashivappa Najare (4) orcid , Mohammed Yaseen (5) orcid , Aravind Raviraj Nesaragi (6) orcid , Sanjeev Ramchandra Inamdar (7) orcid , Imtiyaz Ahmed Khazi (8) orcid , Ravindra Ramappa Kamble (9,*) orcid

(1) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(2) Laser Spectroscopy Program, Department of Physics, Karnatak University, Dharwad, 580003, India
(3) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(4) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(5) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(6) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(7) Laser Spectroscopy Program, Department of Physics, Karnatak University, Dharwad, 580003, India
(8) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(9) Department of Chemistry, Karnatak University, Dharwad 580003, Karnataka, India
(*) Corresponding Author

Received: 12 Aug 2022 | Revised: 25 Nov 2022 | Accepted: 30 Nov 2022 | Published: 31 Mar 2023 | Issue Date: March 2023


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 T5d temperature range from 335 to 354 °C. The cyclic voltammetry study confirms that the Eoxonset 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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European Journal of Chemistry


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

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DOI: 10.5155/eurjchem.14.1.16-29.2320

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Funding information

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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How to cite

Mantur, S.; Patil, M.; Nadaf, A.; Najare, M.; Yaseen, M.; Nesaragi, A.; Inamdar, S.; Khazi, I.; Kamble, R. Eur. J. Chem. 2023, 14(1), 16-29. doi:10.5155/eurjchem.14.1.16-29.2320
Mantur, S.; Patil, M.; Nadaf, A.; Najare, M.; Yaseen, M.; Nesaragi, A.; Inamdar, S.; Khazi, I.; Kamble, R. Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies. Eur. J. Chem. 2023, 14(1), 16-29. doi:10.5155/eurjchem.14.1.16-29.2320
Mantur, S., Patil, M., Nadaf, A., Najare, M., Yaseen, M., Nesaragi, A., Inamdar, S., Khazi, I., & Kamble, R. (2023). Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies. European Journal of Chemistry, 14(1), 16-29. doi:10.5155/eurjchem.14.1.16-29.2320
Mantur, Shivaraj, Mallikarjun Kalagouda Patil, Afra Quasar Abdul Rasheed Nadaf, Mahesh Sadashivappa Najare, Mohammed Yaseen, Aravind Raviraj Nesaragi, Sanjeev Ramchandra Inamdar, Imtiyaz Ahmed Khazi, & Ravindra Ramappa Kamble. "Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies." European Journal of Chemistry [Online], 14.1 (2023): 16-29. Web. 24 Sep. 2023
Mantur, Shivaraj, Patil, Mallikarjun, Nadaf, Afra, Najare, Mahesh, Yaseen, Mohammed, Nesaragi, Aravind, Inamdar, Sanjeev, Khazi, Imtiyaz, AND Kamble, Ravindra. "Orange to red emissive aldehyde substituted donor-π-acceptor phenothiazine derivatives: Optoelectronic, DFT and thermal studies" European Journal of Chemistry [Online], Volume 14 Number 1 (31 March 2023)

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