Synthesis, characterization and density functional theory study of low cost hydrazone sensitizers

Handle URI:
http://hdl.handle.net/10754/599841
Title:
Synthesis, characterization and density functional theory study of low cost hydrazone sensitizers
Authors:
G. Al-Sehemi, A.; Irfan, A.; M. Asiri, A.; A. Ammar, Y.
Abstract:
© 2015 Chemical Society of Ethiopia The 2-{4-[2-benzylidenehydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 1), 2-{4-[2-(1- naphthylmethylene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 2) and 2-{4-[2-(9-anthrylmethylene)- hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 3) were synthesized by direct tricyanovinylation of hydrazones. The bathochromic shift in absorption spectra has been observed by increasing the solvent polarity. The FTIR spectra of these new dyes exhibited three important absorption bands. The first band centered near 3260 cm-1 in System 1 while 3208 cm-1 and 3211 cm-1 in System 2 and System 3 for the vNH absorption, respectively. The second band is a sharp absorption band in the region of 2212-2209 cm-1, which was attributed to the cyano group absorption. The third is an absorption band in the region of 1611-1603 cm-1 ascribed for the C=N. Density functional theory (DFT) calculation of relative energies, relative enthalpies and free energies shows that E isomers are the most stable except System 3 in which the most stable is Z isomers. The conformational energy profile shows two maxima near (-90 and 90°) while three local minima observed at (-180, 0 and 180) for N1-N2-C1-C2 torsional angle. The highest occupied molecular orbitals (HOMOs) are localized on the whole molecules while lowest unoccupied molecular orbitals (LUMOs) are distributed on the tricarbonitrile.
Citation:
G. Al-Sehemi A, Irfan A, M. Asiri A, A. Ammar Y (2015) Synthesis, characterization and density functional theory study of low cost hydrazone sensitizers. Bull Chem Soc Eth 29: 137. Available: http://dx.doi.org/10.4314/bcse.v29i1.13.
Publisher:
African Journals Online (AJOL)
Journal:
Bulletin of the Chemical Society of Ethiopia
KAUST Grant Number:
08-NAN155-7
Issue Date:
18-Jan-2015
DOI:
10.4314/bcse.v29i1.13
Type:
Article
ISSN:
1011-3924
Sponsors:
The present work has been carried out under project No. 08-NAN155-7 funded by KAUST
Appears in Collections:
Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorG. Al-Sehemi, A.en
dc.contributor.authorIrfan, A.en
dc.contributor.authorM. Asiri, A.en
dc.contributor.authorA. Ammar, Y.en
dc.date.accessioned2016-02-28T06:11:05Zen
dc.date.available2016-02-28T06:11:05Zen
dc.date.issued2015-01-18en
dc.identifier.citationG. Al-Sehemi A, Irfan A, M. Asiri A, A. Ammar Y (2015) Synthesis, characterization and density functional theory study of low cost hydrazone sensitizers. Bull Chem Soc Eth 29: 137. Available: http://dx.doi.org/10.4314/bcse.v29i1.13.en
dc.identifier.issn1011-3924en
dc.identifier.doi10.4314/bcse.v29i1.13en
dc.identifier.urihttp://hdl.handle.net/10754/599841en
dc.description.abstract© 2015 Chemical Society of Ethiopia The 2-{4-[2-benzylidenehydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 1), 2-{4-[2-(1- naphthylmethylene)hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 2) and 2-{4-[2-(9-anthrylmethylene)- hydrazino]phenyl}ethylene-1,1,2-tricarbonitrile (System 3) were synthesized by direct tricyanovinylation of hydrazones. The bathochromic shift in absorption spectra has been observed by increasing the solvent polarity. The FTIR spectra of these new dyes exhibited three important absorption bands. The first band centered near 3260 cm-1 in System 1 while 3208 cm-1 and 3211 cm-1 in System 2 and System 3 for the vNH absorption, respectively. The second band is a sharp absorption band in the region of 2212-2209 cm-1, which was attributed to the cyano group absorption. The third is an absorption band in the region of 1611-1603 cm-1 ascribed for the C=N. Density functional theory (DFT) calculation of relative energies, relative enthalpies and free energies shows that E isomers are the most stable except System 3 in which the most stable is Z isomers. The conformational energy profile shows two maxima near (-90 and 90°) while three local minima observed at (-180, 0 and 180) for N1-N2-C1-C2 torsional angle. The highest occupied molecular orbitals (HOMOs) are localized on the whole molecules while lowest unoccupied molecular orbitals (LUMOs) are distributed on the tricarbonitrile.en
dc.description.sponsorshipThe present work has been carried out under project No. 08-NAN155-7 funded by KAUSTen
dc.publisherAfrican Journals Online (AJOL)en
dc.subjectAbsorptionen
dc.subjectDye-sensitized solar cellsen
dc.subjectFTIR spectraen
dc.subjectHOMOen
dc.subjectLUMOen
dc.titleSynthesis, characterization and density functional theory study of low cost hydrazone sensitizersen
dc.typeArticleen
dc.identifier.journalBulletin of the Chemical Society of Ethiopiaen
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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