2 H-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor

Kerba S More; Harshad A Mirgane; Salman Shaikh; Vijayanand Perupogu; Shailesh S Birajdar; Avinash L Puyad; Sidhanath V Bhosale; Sheshanath V Bhosale

doi:10.1021/acs.joc.2c01439

2 H-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor

J Org Chem. 2022 Dec 19. doi: 10.1021/acs.joc.2c01439. Online ahead of print.

Authors

Kerba S More¹, Harshad A Mirgane¹, Salman Shaikh², Vijayanand Perupogu³, Shailesh S Birajdar⁴, Avinash L Puyad², Sidhanath V Bhosale⁴, Sheshanath V Bhosale¹

Affiliations

¹ School of Chemical Sciences, Goa University, Taleigao Plateau 403206, Goa, India.
² School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded 431606, Maharashtra, India.
³ Energy and Environmental Engineering Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.
⁴ Polymers and Functional Materials Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.

PMID: 36534041
DOI: 10.1021/acs.joc.2c01439

Abstract

In this work, a 2H-pyran-2-one-functionalized diketopyrrolopyrrole (DPP) (coded as receptor 1) was designed, synthesized, and fully characterized by various spectroscopic methods. The physical properties of molecular architecture 1 were studied employing theoretical calculations. Receptor 1 was elegantly scrutinized for the sensing of explosive nitroaromatic compounds (NACs). Receptor 1 exhibited detection of nitro explosives, i.e., picric acid (PA), 2,4-dinitrophenol (DNP), and nitrophenol (NP), via the fluorescence quenching mechanism. The Stern-Volmer equation was employed to evaluate the effectiveness of the quenching process. It was found that 1 exhibited a detection limit of about 7.58 × 10^-5, 8.35 × 10^-5, and 9.05 × 10^-5 M toward PA, DNP, and NP, respectively. The influence of interfering metal ions and anions on PA detection was investigated thoroughly. Furthermore, receptor 1-based low-cost fluorescent thin-layer chromatography (TLC) plates were developed for the recognition of PA.