Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study

Handle URI:
http://hdl.handle.net/10754/598873
Title:
Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study
Authors:
Al-Sehemi, Abdullah G.; Irfan, Ahmad; Asiri, Abdullah M.; Ammar, Yousry Ahmed
Abstract:
Three new sensitizers 2-{4-[2-(4-Nitrobenzylidene)hydrazino)]phenyl} ethylene-1,1,2-tricarbonitrile (NBHPET), 2-{4-[2-p-Chlorobenzylidenehydrazino] phenyl}- ethylene-1,1,2-tri carbonitrile (CBHPET) and 2-{4-[2-p- Bromobenzylidenehydrazino] phenyl}ethylene-1,1,2-tricarbonitrile (BBHPET) have been synthesized. The dyes showed pronounced solvatochromic effects as the polarity of the solvents increased. The structures have been optimized at B3LYP/6-31G(d) level of theory. The torsion in E-isomer is smaller than Z-isomer and azo isomers. The highest occupied molecular orbitals are delocalized on whole molecule while lowest unoccupied molecular orbitals are distributed on the tricarbonitrile. The lowest unoccupied molecular orbital energies are above the conduction band of titanium dioxide, highest occupied molecular orbitals of the dyes are below the redox couple of new synthesized dyes and small energy gap revealed these dyes would be better sensitizers for dye-sensitized solar cells. © 2012 Elsevier B.V. All rights reserved.
Citation:
Al-Sehemi AG, Irfan A, Asiri AM, Ammar YA (2012) Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study. Journal of Molecular Structure 1019: 130–134. Available: http://dx.doi.org/10.1016/j.molstruc.2012.02.035.
Publisher:
Elsevier BV
Journal:
Journal of Molecular Structure
KAUST Grant Number:
08-NAN155-7
Issue Date:
Jul-2012
DOI:
10.1016/j.molstruc.2012.02.035
Type:
Article
ISSN:
0022-2860
Sponsors:
The present work has been carried out under Project No. 08-NAN155-7 funded by KAUST (King Abdul Aziz City for Science and Technology) through the Long Term Comprehensive National Plan for Science, Technology and Innovation program.
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorAl-Sehemi, Abdullah G.en
dc.contributor.authorIrfan, Ahmaden
dc.contributor.authorAsiri, Abdullah M.en
dc.contributor.authorAmmar, Yousry Ahmeden
dc.date.accessioned2016-02-25T13:42:51Zen
dc.date.available2016-02-25T13:42:51Zen
dc.date.issued2012-07en
dc.identifier.citationAl-Sehemi AG, Irfan A, Asiri AM, Ammar YA (2012) Molecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT study. Journal of Molecular Structure 1019: 130–134. Available: http://dx.doi.org/10.1016/j.molstruc.2012.02.035.en
dc.identifier.issn0022-2860en
dc.identifier.doi10.1016/j.molstruc.2012.02.035en
dc.identifier.urihttp://hdl.handle.net/10754/598873en
dc.description.abstractThree new sensitizers 2-{4-[2-(4-Nitrobenzylidene)hydrazino)]phenyl} ethylene-1,1,2-tricarbonitrile (NBHPET), 2-{4-[2-p-Chlorobenzylidenehydrazino] phenyl}- ethylene-1,1,2-tri carbonitrile (CBHPET) and 2-{4-[2-p- Bromobenzylidenehydrazino] phenyl}ethylene-1,1,2-tricarbonitrile (BBHPET) have been synthesized. The dyes showed pronounced solvatochromic effects as the polarity of the solvents increased. The structures have been optimized at B3LYP/6-31G(d) level of theory. The torsion in E-isomer is smaller than Z-isomer and azo isomers. The highest occupied molecular orbitals are delocalized on whole molecule while lowest unoccupied molecular orbitals are distributed on the tricarbonitrile. The lowest unoccupied molecular orbital energies are above the conduction band of titanium dioxide, highest occupied molecular orbitals of the dyes are below the redox couple of new synthesized dyes and small energy gap revealed these dyes would be better sensitizers for dye-sensitized solar cells. © 2012 Elsevier B.V. All rights reserved.en
dc.description.sponsorshipThe present work has been carried out under Project No. 08-NAN155-7 funded by KAUST (King Abdul Aziz City for Science and Technology) through the Long Term Comprehensive National Plan for Science, Technology and Innovation program.en
dc.publisherElsevier BVen
dc.subjectAbsorptionen
dc.subjectDensity functional theoryen
dc.subjectDye-sensitized solar cellsen
dc.subjectTransport propertiesen
dc.titleMolecular design of new hydrazone dyes for dye-sensitized solar cells: Synthesis, characterization and DFT studyen
dc.typeArticleen
dc.identifier.journalJournal of Molecular Structureen
dc.contributor.institutionKing Khalid University, Abha, Saudi Arabiaen
dc.contributor.institutionKing Abdulaziz University, Jeddah, Saudi Arabiaen
kaust.grant.number08-NAN155-7en
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