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Title: Transforming Benzophenoxazine Laser Dyes into Chromophores for Dye-Sensitized Solar Cells: A Molecular Engineering Approach

Abstract

The re-functionalization of a series of four well-known industrial laser dyes, based on benzophenoxazine, is explored with the prospect of molecularly engineering new chromophores for dye-sensitized solar cell (DSC) applications. Such engineering is important since a lack of suitable dyes is stifling the progress of DSC technology. The conceptual idea involves making laser dyes DSC-active by chemical modification, while maintaining their key property attributes that are attractive to DSC applications. This molecular engineering follows a step-wise approach. Firstly, molecular structures and optical absorption properties are determined for the parent laser dyes: Cresyl Violet (1); Oxazine 170 (2); Nile Blue A (3), Oxazine 750 (4). These reveal structure-property relationships which define the prerequisites for computational molecular design of DSC dyes; the nature of their molecular architecture (D-π-A) and intramolecular charge transfer. Secondly, new DSC dyes are computationally designed by the in silico addition of a carboxylic acid anchor at various chemical substitution points in the parent laser dyes. A comparison of the resulting frontier molecular orbital energy levels with the conduction band edge of a TiO2 DSC photoanode and the redox potential of two electrolyte options I-/I3- and Co(II/III)tris(bipyridyl) suggests promise for these computationally designed dyes as co-sensitizers for DSC applications.

Authors:
 [1];  [2];  [3];  [1]
  1. Cavendish Laboratory, University of Cambridge, J. J. Thomson Avenue Cambridge CB3 0HE UK
  2. Cavendish Laboratory, University of Cambridge, J. J. Thomson Avenue Cambridge CB3 0HE UK; Argonne National Laboratory, 9700 S. Cass Avenue Argonne IL 60439 USA; International Institute for Complex Adaptive Matter, University of California Davis, Davis CA 95616 USA
  3. Cavendish Laboratory, University of Cambridge, J. J. Thomson Avenue Cambridge CB3 0HE UK; Australian Nuclear Science and Technology Organization, Lucas Heights, New South Wales 2234 Australia
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science - Office of Basic Energy Sciences - Materials Sciences and Engineering Division
OSTI Identifier:
1392616
DOE Contract Number:  
AC02-06CH11357
Resource Type:
Journal Article
Resource Relation:
Journal Name: Advanced Energy Materials; Journal Volume: 5; Journal Issue: 9
Country of Publication:
United States
Language:
English
Subject:
dye co-sensitization; dye-sensitized solar cells; laser dyes; molecular engineering; structure-property relationships

Citation Formats

Schröder, Florian A. Y. N., Cole, Jacqueline M., Waddell, Paul G., and McKechnie, Scott. Transforming Benzophenoxazine Laser Dyes into Chromophores for Dye-Sensitized Solar Cells: A Molecular Engineering Approach. United States: N. p., 2015. Web. doi:10.1002/aenm.201401728.
Schröder, Florian A. Y. N., Cole, Jacqueline M., Waddell, Paul G., & McKechnie, Scott. Transforming Benzophenoxazine Laser Dyes into Chromophores for Dye-Sensitized Solar Cells: A Molecular Engineering Approach. United States. doi:10.1002/aenm.201401728.
Schröder, Florian A. Y. N., Cole, Jacqueline M., Waddell, Paul G., and McKechnie, Scott. Tue . "Transforming Benzophenoxazine Laser Dyes into Chromophores for Dye-Sensitized Solar Cells: A Molecular Engineering Approach". United States. doi:10.1002/aenm.201401728.
@article{osti_1392616,
title = {Transforming Benzophenoxazine Laser Dyes into Chromophores for Dye-Sensitized Solar Cells: A Molecular Engineering Approach},
author = {Schröder, Florian A. Y. N. and Cole, Jacqueline M. and Waddell, Paul G. and McKechnie, Scott},
abstractNote = {The re-functionalization of a series of four well-known industrial laser dyes, based on benzophenoxazine, is explored with the prospect of molecularly engineering new chromophores for dye-sensitized solar cell (DSC) applications. Such engineering is important since a lack of suitable dyes is stifling the progress of DSC technology. The conceptual idea involves making laser dyes DSC-active by chemical modification, while maintaining their key property attributes that are attractive to DSC applications. This molecular engineering follows a step-wise approach. Firstly, molecular structures and optical absorption properties are determined for the parent laser dyes: Cresyl Violet (1); Oxazine 170 (2); Nile Blue A (3), Oxazine 750 (4). These reveal structure-property relationships which define the prerequisites for computational molecular design of DSC dyes; the nature of their molecular architecture (D-π-A) and intramolecular charge transfer. Secondly, new DSC dyes are computationally designed by the in silico addition of a carboxylic acid anchor at various chemical substitution points in the parent laser dyes. A comparison of the resulting frontier molecular orbital energy levels with the conduction band edge of a TiO2 DSC photoanode and the redox potential of two electrolyte options I-/I3- and Co(II/III)tris(bipyridyl) suggests promise for these computationally designed dyes as co-sensitizers for DSC applications.},
doi = {10.1002/aenm.201401728},
journal = {Advanced Energy Materials},
number = 9,
volume = 5,
place = {United States},
year = {Tue Feb 03 00:00:00 EST 2015},
month = {Tue Feb 03 00:00:00 EST 2015}
}