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

Siti Nabilla Aliya Mohd Nizar,Ainizatul Husna Anizaim,Muhamad Fikri Zaini,Suhana Arshad,Siti Noor Farhana Ab Rahman,Ibrahim Abdul Razak

doi:10.3390/cryst11111357

Siti Nabilla Aliya Mohd Nizar, Ainizatul Husna Anizaim + Show 4 more

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https://doi.org/10.3390/cryst11111357

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Abstract

Two newly halogenated chalcones, derivatives of C15H10ClFO (CH-ClF) and C15H10F2O (CH-FF), 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 P21 and P21/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 CH-FF. 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 CH-FF, 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).

Highlights

There has been much research into organic material due to its variety of design selections, which can be used with suitable reactants through simple procedures and low synthesis cost [1,2]
The Fourier Transform Infrared (FTIR) spectra of CH-ClF and CH-Fill Factor (FF) from the experimental analysis are depicted in Figure 3 reported and summarized in Table
The compound with the highest electronegative properties (CH-FF) was able to enhance the charge transfer flow inside the molecules compared to the compound with lower electronegativity (CHClF)

Summary

Introduction

There has been much research into organic material due to its variety of design selections, which can be used with suitable reactants through simple procedures and low synthesis cost [1,2]. Chalcones are organic materials from the flavonoid family with a molecular structure that can be modified and synthesized using assorted heterocyclic compounds [3]. As the substituent components of chalcone can be varied, this leads to spectroscopic and characterization analysis regarding structural planarity, the involvement of intermolecular interaction, and the intramolecular charge transfer (ICT) of the compounds [5]. Acceptor (A) linked via the α, β- unsaturated keto group as D–A–D, A–D–A, D–π–A, D–π–D and A–π–A construct a chalcone with a good charge transfer configuration for use as a dye-sensitizer in solar cell applications [6,7,8]. Many researchers have employed chalcone derivatives as sensitizers [9,10,11,12,13,14] due to their properties and performance. The ability of various substituents to be anchored at different positions in chalcone derivatives enables studies on their light harvesting potential

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