The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

Two newly halogenated chalcones, derivatives of C15H10ClFO (CH-ClF) and C15H10F2O (CH-FF), were synthesized using the Claisen–Schmidt condensation...

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Autores principales:	Siti Nabilla Aliya Mohd Nizar, Siti Noor Farhana Ab Rahman, Muhamad Fikri Zaini, Ainizatul Husna Anizaim, Ibrahim Abdul Razak, Suhana Arshad
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	halogenated chalcone single crystal DFT A-π-A organic dye DSSC Crystallography QD901-999
Acceso en línea:	https://doaj.org/article/cfb79789d21749fca50c064578474de8
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spelling	oai:doaj.org-article:cfb79789d21749fca50c064578474de82021-11-25T17:18:47ZThe Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents10.3390/cryst111113572073-4352https://doaj.org/article/cfb79789d21749fca50c064578474de82021-11-01T00:00:00Zhttps://www.mdpi.com/2073-4352/11/11/1357https://doaj.org/toc/2073-4352Two newly halogenated chalcones, derivatives of C<sub>15</sub>H<sub>10</sub>ClFO (<b>CH-ClF</b>) and C<sub>15</sub>H<sub>10</sub>F<sub>2</sub>O (<b>CH-FF</b>), were synthesized using the Claisen–Schmidt condensation method. Both compounds were crystallized using a slow evaporation method, forming a monoclinic crystal system with a space group of P2<sub>1</sub> and P2<sub>1</sub>/c, respectively. The compounds were further analyzed using spectroscopic techniques such as Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR), and Ultraviolet–Visible (UV–vis) analyses. The single crystal X-ray diffraction method revealed the existence of C−H⋯O and C−H⋯F intermolecular interactions in <b>CH-FF</b>. Hirshfeld surface analysis was performed to confirm the existence of intermolecular interactions in the compounds. The molecular geometries obtained from the X-ray structure determination were further used to optimize the structures using density functional theory (DFT), with the B3LYP/6-311G++(d,p) basis set in the ground state. The TD-DFT/B3LYP method was used to obtain the electronic properties and the HOMO–LUMO energy gap. Both compounds exhibited A-π-A architecture with different halogen substituents in which the <b>CH-FF</b>, containing -fluoro substituents, possessed good electron injection ability due to its electronegative properties. This increased the flow of the charge transfer for the dye regeneration process and enhanced the efficiency of the dye-sensitized solar cell (DSSC).Siti Nabilla Aliya Mohd NizarSiti Noor Farhana Ab RahmanMuhamad Fikri ZainiAinizatul Husna AnizaimIbrahim Abdul RazakSuhana ArshadMDPI AGarticlehalogenated chalconesingle crystalDFTA-π-A organic dyeDSSCCrystallographyQD901-999ENCrystals, Vol 11, Iss 1357, p 1357 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	halogenated chalcone single crystal DFT A-π-A organic dye DSSC Crystallography QD901-999
spellingShingle	halogenated chalcone single crystal DFT A-π-A organic dye DSSC Crystallography QD901-999 Siti Nabilla Aliya Mohd Nizar Siti Noor Farhana Ab Rahman Muhamad Fikri Zaini Ainizatul Husna Anizaim Ibrahim Abdul Razak Suhana Arshad The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
description	Two newly halogenated chalcones, derivatives of C<sub>15</sub>H<sub>10</sub>ClFO (<b>CH-ClF</b>) and C<sub>15</sub>H<sub>10</sub>F<sub>2</sub>O (<b>CH-FF</b>), were synthesized using the Claisen–Schmidt condensation method. Both compounds were crystallized using a slow evaporation method, forming a monoclinic crystal system with a space group of P2<sub>1</sub> and P2<sub>1</sub>/c, respectively. The compounds were further analyzed using spectroscopic techniques such as Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR), and Ultraviolet–Visible (UV–vis) analyses. The single crystal X-ray diffraction method revealed the existence of C−H⋯O and C−H⋯F intermolecular interactions in <b>CH-FF</b>. Hirshfeld surface analysis was performed to confirm the existence of intermolecular interactions in the compounds. The molecular geometries obtained from the X-ray structure determination were further used to optimize the structures using density functional theory (DFT), with the B3LYP/6-311G++(d,p) basis set in the ground state. The TD-DFT/B3LYP method was used to obtain the electronic properties and the HOMO–LUMO energy gap. Both compounds exhibited A-π-A architecture with different halogen substituents in which the <b>CH-FF</b>, containing -fluoro substituents, possessed good electron injection ability due to its electronegative properties. This increased the flow of the charge transfer for the dye regeneration process and enhanced the efficiency of the dye-sensitized solar cell (DSSC).
format	article
author	Siti Nabilla Aliya Mohd Nizar Siti Noor Farhana Ab Rahman Muhamad Fikri Zaini Ainizatul Husna Anizaim Ibrahim Abdul Razak Suhana Arshad
author_facet	Siti Nabilla Aliya Mohd Nizar Siti Noor Farhana Ab Rahman Muhamad Fikri Zaini Ainizatul Husna Anizaim Ibrahim Abdul Razak Suhana Arshad
author_sort	Siti Nabilla Aliya Mohd Nizar
title	The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
title_short	The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
title_full	The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
title_fullStr	The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
title_full_unstemmed	The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents
title_sort	photovoltaic performance of sensitizers for organic solar cells containing fluorinated chalcones with different halogen substituents
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/cfb79789d21749fca50c064578474de8
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The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

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