Synthesis and characterization of a thienopyrazine-based low band-gap poly(arylene ethynylene) and photocell studies of the poly-yne/perylene dye blend with broad photocurrent spectrum

Maharaja Jayapal, Ashanul Haque, Idris J. Al-Busaidi, Rayya Al-Balushi, Mohammed K. Al-Suti, Shahidul M. Islam, Muhammad S. Khan, Janke J. Dittmer

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Background: In the quest for sustainable energy materials, new donor and acceptor materials are being designed, synthesized and tested for photovoltaic (PV) applications. In this context, conjugated organic polymers have received significant interests in the last few decades. Objective: In the present work, we synthesized an organic poly-yne P and assessed its efficiency as donor with a rylene acceptor EP-PTC. Methods: The organic poly-yne P was synthesised via Sonogashira coupling and characterized by analytical and spectroscopic techniques. The PV performance of blends composed of different amounts of polymer P and acceptor EP-PTC was assessed. Computational studies were undertaken at DFT level to determine the geometry, dipole moment, Mulliken charge and energy level. Results: A soluble blue low band-gap (1.72 eV) π-conjugated co-polymer consisting of dioctyloxyphenylene unit linked via ethynylene to 2,3-diphenylthieno[3,4-b]pyrazine has been synthesized and characterized. Blends of P and a soluble organic dye EP-PTC showed good PV performance with broad photocurrent spectra. The copoly-yne/dye-based solar cell with high EP-PTC content shows significantly higher external quantum efficiency (EQE) compared to the single material-based devices. However, a decrease in EQE was observed upon thermal annealing. DFT calculations showed convergence of the experimental results. Conclusion: We have synthesized and characterized a thienopyrazine-based organic co-polyyne and showed that blends of co-polymer P and the perylene dye EP-PTC possess high EQE up to 5.5% for the 90: 10 EPPTC: P blend at wavelengths between 350 nm and 710 nm.

Original languageEnglish
Pages (from-to)2017-2027
Number of pages11
JournalCurrent Organic Chemistry
Volume21
Issue number19
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Perylene
Photoelectric cells
Factor IX
Photocurrents
Energy gap
Coloring Agents
Quantum efficiency
Polymers
Discrete Fourier transforms
Pyrazines
Organic polymers
Conjugated polymers
Dipole moment
Electron energy levels
Solar cells
Annealing
Wavelength
Geometry

Keywords

  • Blend
  • DFT
  • EQE
  • Organic poly-yne
  • Perylene
  • Thermal annealing

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and characterization of a thienopyrazine-based low band-gap poly(arylene ethynylene) and photocell studies of the poly-yne/perylene dye blend with broad photocurrent spectrum. / Jayapal, Maharaja; Haque, Ashanul; Al-Busaidi, Idris J.; Al-Balushi, Rayya; Al-Suti, Mohammed K.; Islam, Shahidul M.; Khan, Muhammad S.; Dittmer, Janke J.

In: Current Organic Chemistry, Vol. 21, No. 19, 01.01.2017, p. 2017-2027.

Research output: Contribution to journalArticle

Jayapal, Maharaja ; Haque, Ashanul ; Al-Busaidi, Idris J. ; Al-Balushi, Rayya ; Al-Suti, Mohammed K. ; Islam, Shahidul M. ; Khan, Muhammad S. ; Dittmer, Janke J. / Synthesis and characterization of a thienopyrazine-based low band-gap poly(arylene ethynylene) and photocell studies of the poly-yne/perylene dye blend with broad photocurrent spectrum. In: Current Organic Chemistry. 2017 ; Vol. 21, No. 19. pp. 2017-2027.
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abstract = "Background: In the quest for sustainable energy materials, new donor and acceptor materials are being designed, synthesized and tested for photovoltaic (PV) applications. In this context, conjugated organic polymers have received significant interests in the last few decades. Objective: In the present work, we synthesized an organic poly-yne P and assessed its efficiency as donor with a rylene acceptor EP-PTC. Methods: The organic poly-yne P was synthesised via Sonogashira coupling and characterized by analytical and spectroscopic techniques. The PV performance of blends composed of different amounts of polymer P and acceptor EP-PTC was assessed. Computational studies were undertaken at DFT level to determine the geometry, dipole moment, Mulliken charge and energy level. Results: A soluble blue low band-gap (1.72 eV) π-conjugated co-polymer consisting of dioctyloxyphenylene unit linked via ethynylene to 2,3-diphenylthieno[3,4-b]pyrazine has been synthesized and characterized. Blends of P and a soluble organic dye EP-PTC showed good PV performance with broad photocurrent spectra. The copoly-yne/dye-based solar cell with high EP-PTC content shows significantly higher external quantum efficiency (EQE) compared to the single material-based devices. However, a decrease in EQE was observed upon thermal annealing. DFT calculations showed convergence of the experimental results. Conclusion: We have synthesized and characterized a thienopyrazine-based organic co-polyyne and showed that blends of co-polymer P and the perylene dye EP-PTC possess high EQE up to 5.5{\%} for the 90: 10 EPPTC: P blend at wavelengths between 350 nm and 710 nm.",
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T1 - Synthesis and characterization of a thienopyrazine-based low band-gap poly(arylene ethynylene) and photocell studies of the poly-yne/perylene dye blend with broad photocurrent spectrum

AU - Jayapal, Maharaja

AU - Haque, Ashanul

AU - Al-Busaidi, Idris J.

AU - Al-Balushi, Rayya

AU - Al-Suti, Mohammed K.

AU - Islam, Shahidul M.

AU - Khan, Muhammad S.

AU - Dittmer, Janke J.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - Background: In the quest for sustainable energy materials, new donor and acceptor materials are being designed, synthesized and tested for photovoltaic (PV) applications. In this context, conjugated organic polymers have received significant interests in the last few decades. Objective: In the present work, we synthesized an organic poly-yne P and assessed its efficiency as donor with a rylene acceptor EP-PTC. Methods: The organic poly-yne P was synthesised via Sonogashira coupling and characterized by analytical and spectroscopic techniques. The PV performance of blends composed of different amounts of polymer P and acceptor EP-PTC was assessed. Computational studies were undertaken at DFT level to determine the geometry, dipole moment, Mulliken charge and energy level. Results: A soluble blue low band-gap (1.72 eV) π-conjugated co-polymer consisting of dioctyloxyphenylene unit linked via ethynylene to 2,3-diphenylthieno[3,4-b]pyrazine has been synthesized and characterized. Blends of P and a soluble organic dye EP-PTC showed good PV performance with broad photocurrent spectra. The copoly-yne/dye-based solar cell with high EP-PTC content shows significantly higher external quantum efficiency (EQE) compared to the single material-based devices. However, a decrease in EQE was observed upon thermal annealing. DFT calculations showed convergence of the experimental results. Conclusion: We have synthesized and characterized a thienopyrazine-based organic co-polyyne and showed that blends of co-polymer P and the perylene dye EP-PTC possess high EQE up to 5.5% for the 90: 10 EPPTC: P blend at wavelengths between 350 nm and 710 nm.

AB - Background: In the quest for sustainable energy materials, new donor and acceptor materials are being designed, synthesized and tested for photovoltaic (PV) applications. In this context, conjugated organic polymers have received significant interests in the last few decades. Objective: In the present work, we synthesized an organic poly-yne P and assessed its efficiency as donor with a rylene acceptor EP-PTC. Methods: The organic poly-yne P was synthesised via Sonogashira coupling and characterized by analytical and spectroscopic techniques. The PV performance of blends composed of different amounts of polymer P and acceptor EP-PTC was assessed. Computational studies were undertaken at DFT level to determine the geometry, dipole moment, Mulliken charge and energy level. Results: A soluble blue low band-gap (1.72 eV) π-conjugated co-polymer consisting of dioctyloxyphenylene unit linked via ethynylene to 2,3-diphenylthieno[3,4-b]pyrazine has been synthesized and characterized. Blends of P and a soluble organic dye EP-PTC showed good PV performance with broad photocurrent spectra. The copoly-yne/dye-based solar cell with high EP-PTC content shows significantly higher external quantum efficiency (EQE) compared to the single material-based devices. However, a decrease in EQE was observed upon thermal annealing. DFT calculations showed convergence of the experimental results. Conclusion: We have synthesized and characterized a thienopyrazine-based organic co-polyyne and showed that blends of co-polymer P and the perylene dye EP-PTC possess high EQE up to 5.5% for the 90: 10 EPPTC: P blend at wavelengths between 350 nm and 710 nm.

KW - Blend

KW - DFT

KW - EQE

KW - Organic poly-yne

KW - Perylene

KW - Thermal annealing

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