Synthesis, characterization and DFT study of methoxybenzylidene containing chromophores for DSSC materials

Abdullah G. Al-Sehemi; Ahmad Irfan; Abdullah M. Asiri; Yousry Ahmed Ammar

doi:10.1016/j.saa.2012.01.016

Synthesis, characterization and DFT study of methoxybenzylidene containing chromophores for DSSC materials

Abdullah G. Al-Sehemi, Ahmad Irfan, Abdullah M. Asiri, Yousry Ahmed Ammar

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52 Scopus citations

Abstract

Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 539-650 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents changed. The torsion in E isomer is smaller than Z and azo isomers of MBD1 and MBD2. The HOMOs are delocalized on whole of the molecule while LUMOs are distributed on the tricarbonitrile. The LUMO energies are above the conduction band of TiO 2 and HOMOs of the dyes are below the redox couple of MBD1 and MBD2. The HOMO energies, LUMO energies and HOMO-LUMO energy gap of MBD1 and MBD2 are almost same. The absorption spectra of both the dyes in different solvents are approximately same except in cyclohexane. © 2012 Elsevier B.V. All rights reserved.

Original language	English (US)
Pages (from-to)	239-243
Number of pages	5
Journal	Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Volume	91
DOIs	https://doi.org/10.1016/j.saa.2012.01.016
State	Published - Jun 2012
Externally published	Yes

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): 08-NAN155-7
Acknowledgements: The present work has been carried out under project No. 08-NAN155-7 funded by KAUST (King Abdulaziz City for Science and Technology) through the Long Term Comprehensive National Plan for Science, Technology and Innovation program.
This publication acknowledges KAUST support, but has no KAUST affiliated authors.

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title = "Synthesis, characterization and DFT study of methoxybenzylidene containing chromophores for DSSC materials",

abstract = "Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 539-650 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents changed. The torsion in E isomer is smaller than Z and azo isomers of MBD1 and MBD2. The HOMOs are delocalized on whole of the molecule while LUMOs are distributed on the tricarbonitrile. The LUMO energies are above the conduction band of TiO 2 and HOMOs of the dyes are below the redox couple of MBD1 and MBD2. The HOMO energies, LUMO energies and HOMO-LUMO energy gap of MBD1 and MBD2 are almost same. The absorption spectra of both the dyes in different solvents are approximately same except in cyclohexane. {\textcopyright} 2012 Elsevier B.V. All rights reserved.",

author = "Al-Sehemi, {Abdullah G.} and Ahmad Irfan and Asiri, {Abdullah M.} and Ammar, {Yousry Ahmed}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): 08-NAN155-7 Acknowledgements: The present work has been carried out under project No. 08-NAN155-7 funded by KAUST (King Abdulaziz City for Science and Technology) through the Long Term Comprehensive National Plan for Science, Technology and Innovation program. This publication acknowledges KAUST support, but has no KAUST affiliated authors.",

year = "2012",

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doi = "10.1016/j.saa.2012.01.016",

language = "English (US)",

volume = "91",

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journal = "Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy",

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AU - Al-Sehemi, Abdullah G.

AU - Irfan, Ahmad

AU - Asiri, Abdullah M.

AU - Ammar, Yousry Ahmed

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): 08-NAN155-7 Acknowledgements: The present work has been carried out under project No. 08-NAN155-7 funded by KAUST (King Abdulaziz City for Science and Technology) through the Long Term Comprehensive National Plan for Science, Technology and Innovation program. This publication acknowledges KAUST support, but has no KAUST affiliated authors.

PY - 2012/6

Y1 - 2012/6

N2 - Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 539-650 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents changed. The torsion in E isomer is smaller than Z and azo isomers of MBD1 and MBD2. The HOMOs are delocalized on whole of the molecule while LUMOs are distributed on the tricarbonitrile. The LUMO energies are above the conduction band of TiO 2 and HOMOs of the dyes are below the redox couple of MBD1 and MBD2. The HOMO energies, LUMO energies and HOMO-LUMO energy gap of MBD1 and MBD2 are almost same. The absorption spectra of both the dyes in different solvents are approximately same except in cyclohexane. © 2012 Elsevier B.V. All rights reserved.

AB - Novel tricyanovinyl derived from hydrazones have been prepared by the reaction of tetracyanoethylene and phenylethylidene hydrazone, and these dyes showed absorption in the region of 539-650 nm. The dyes showed pronounced solvatochromic effects as the polarity of the solvents changed. The torsion in E isomer is smaller than Z and azo isomers of MBD1 and MBD2. The HOMOs are delocalized on whole of the molecule while LUMOs are distributed on the tricarbonitrile. The LUMO energies are above the conduction band of TiO 2 and HOMOs of the dyes are below the redox couple of MBD1 and MBD2. The HOMO energies, LUMO energies and HOMO-LUMO energy gap of MBD1 and MBD2 are almost same. The absorption spectra of both the dyes in different solvents are approximately same except in cyclohexane. © 2012 Elsevier B.V. All rights reserved.

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SN - 1386-1425

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EP - 243

JO - Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

ER -

Synthesis, characterization and DFT study of methoxybenzylidene containing chromophores for DSSC materials

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