Synthesis, photophysical and DFT studies of naphthyl chalcone and nicotinonitrile derivatives

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Abstract

Chalcone and cyanopyridine derivatives have emerged as attractive light sensitive materials, with potential use in cell probing and optoelectronic applications. They are highly fluorescent both in solution and solid state and thus well-suited for OLED applications. Herein, we report the synthesis of a chalcone derivative (CP1) using the Claisen Schmidt condensation of 2-acetyl thiophene and 2-methoxy naphthaldehyde followed by the heterocyclization to yield the novel cyanopyridine derivative (NP1). Synthesized molecules were characterized using elemental analysis, FTIR and NMR spectra. Density functional theory (DFT) calculations were performed on the molecules, in order to understand their absorption and emission properties. The orbital picture of all the excitations involved in these transitions were identified as π- > π*. The, experimentally obtained FTIR spectra were in excellent agreement with DFT calculated infrared spectrum. The steady state fluorescence spectra of CP1 showed dual emission in the blue and green regions while a single band, orange emission was observed for the other molecule NC1. NC1 showed the solid-state emission in orange region inferring its suitability for the OLED application.

Original languageEnglish
Article number112222
JournalJournal of Photochemistry and Photobiology A: Chemistry
DOIs
Publication statusAccepted/In press - 01-01-2019

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Chalcone
Density functional theory
Organic light emitting diodes (OLED)
density functional theory
Derivatives
Molecules
Light sensitive materials
synthesis
Thiophenes
Thiophene
solid state
molecules
Optoelectronic devices
Condensation
thiophenes
Fluorescence
Nuclear magnetic resonance
Infrared radiation
infrared spectra
condensation

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)
  • Physics and Astronomy(all)

Cite this

@article{e1f311f2d4f041fb96b73365a1843685,
title = "Synthesis, photophysical and DFT studies of naphthyl chalcone and nicotinonitrile derivatives",
abstract = "Chalcone and cyanopyridine derivatives have emerged as attractive light sensitive materials, with potential use in cell probing and optoelectronic applications. They are highly fluorescent both in solution and solid state and thus well-suited for OLED applications. Herein, we report the synthesis of a chalcone derivative (CP1) using the Claisen Schmidt condensation of 2-acetyl thiophene and 2-methoxy naphthaldehyde followed by the heterocyclization to yield the novel cyanopyridine derivative (NP1). Synthesized molecules were characterized using elemental analysis, FTIR and NMR spectra. Density functional theory (DFT) calculations were performed on the molecules, in order to understand their absorption and emission properties. The orbital picture of all the excitations involved in these transitions were identified as π- > π*. The, experimentally obtained FTIR spectra were in excellent agreement with DFT calculated infrared spectrum. The steady state fluorescence spectra of CP1 showed dual emission in the blue and green regions while a single band, orange emission was observed for the other molecule NC1. NC1 showed the solid-state emission in orange region inferring its suitability for the OLED application.",
author = "Hemant Hegde and Sinha, {Rajeev K.} and Kulkarni, {Suresh D.} and Shetty, {Nitinkumar S.}",
year = "2019",
month = "1",
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doi = "10.1016/j.jphotochem.2019.112222",
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journal = "Journal of Photochemistry and Photobiology A: Chemistry",
issn = "1010-6030",
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AU - Hegde, Hemant

AU - Sinha, Rajeev K.

AU - Kulkarni, Suresh D.

AU - Shetty, Nitinkumar S.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Chalcone and cyanopyridine derivatives have emerged as attractive light sensitive materials, with potential use in cell probing and optoelectronic applications. They are highly fluorescent both in solution and solid state and thus well-suited for OLED applications. Herein, we report the synthesis of a chalcone derivative (CP1) using the Claisen Schmidt condensation of 2-acetyl thiophene and 2-methoxy naphthaldehyde followed by the heterocyclization to yield the novel cyanopyridine derivative (NP1). Synthesized molecules were characterized using elemental analysis, FTIR and NMR spectra. Density functional theory (DFT) calculations were performed on the molecules, in order to understand their absorption and emission properties. The orbital picture of all the excitations involved in these transitions were identified as π- > π*. The, experimentally obtained FTIR spectra were in excellent agreement with DFT calculated infrared spectrum. The steady state fluorescence spectra of CP1 showed dual emission in the blue and green regions while a single band, orange emission was observed for the other molecule NC1. NC1 showed the solid-state emission in orange region inferring its suitability for the OLED application.

AB - Chalcone and cyanopyridine derivatives have emerged as attractive light sensitive materials, with potential use in cell probing and optoelectronic applications. They are highly fluorescent both in solution and solid state and thus well-suited for OLED applications. Herein, we report the synthesis of a chalcone derivative (CP1) using the Claisen Schmidt condensation of 2-acetyl thiophene and 2-methoxy naphthaldehyde followed by the heterocyclization to yield the novel cyanopyridine derivative (NP1). Synthesized molecules were characterized using elemental analysis, FTIR and NMR spectra. Density functional theory (DFT) calculations were performed on the molecules, in order to understand their absorption and emission properties. The orbital picture of all the excitations involved in these transitions were identified as π- > π*. The, experimentally obtained FTIR spectra were in excellent agreement with DFT calculated infrared spectrum. The steady state fluorescence spectra of CP1 showed dual emission in the blue and green regions while a single band, orange emission was observed for the other molecule NC1. NC1 showed the solid-state emission in orange region inferring its suitability for the OLED application.

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