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

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

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

Type

Article

Authors

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

KAUST Grant Number

08-NAN155-7

Date

2012-07

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.

Acknowledgements

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.