DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Chemometric modeling of power conversion efficiency of organic dyes in dye sensitized solar cells for the future renewable energy

Abstract

The present study reports chemometric modeling of power conversion efficiency (PCE) of dye sensitized solar cells (DSSCs) using the biggest available data set till date which comprises around 1200 dyes covering 7 chemical classes. To extract the best structural features required for higher PCE, we have developed multiple partial least squares (PLS) quantitative structure-property relationship (QSPR) models for the Triphenylamine, Phenothiazine, Indoline, Porphyrin, Coumarin, Carbazole and Diphenylamine chemical classes using descriptors derived from the best subset selection method followed by selection of best five models in each dataset based on the Mean Absolute Error (MAE) values. The models were validated both internally and externally followed by the consensus predictions employing “Intelligent Consensus Predictor” tool to examine whether the quality of predictions can be improved with the “intelligent” selection of multiple PLS models. The quality of predictions for the respective external sets showed that the consensus models (CM) are better than the individual models (IM) in most of the cases. From the insights of the developed models, we concluded that attributes like a packed structure toward higher conductivity of electrons, auxiliary donor fragment of aromatic tertiary amines, number of thiophenes inducing the bathochromic shift and augmenting the absorption, presence of additional electron donors, enhancement of electron-donating abilities, number of non-aromatic conjugated C(sp2) which helps as conjugation extension units to broaden the absorption and highly conjugated $$π$$-systems exert positive contributions to the PCE. On the contrary, features negatively contributing to PCE are the followings: fragments which lower the tendency of localized $π–π*$ transition, fragments related to larger volume and surface area of dyes along with hydrophobicity resulting in poor adhesion, fragment RC = N causing dye hydrolysis, steric hindrance for π electronic mobility, fragments enhancing polarity, etc. Finally, the identified features from the best QSPR model of the coumarin dataset was employed in designing of ten more efficient coumarin dyes (predicted %PCE ranging from 8.93 to 10.62) than the existing ones.

Authors:
 [1];  [2];  [3];  [2];  [3]
  1. National Inst. of Pharmaceutical Educational and Research (NIPER), Kolkata (India)
  2. Jadavpur Univ. Kolkata (India)
  3. Jackson State Univ., Jackson, MS (United States)
Publication Date:
Research Org.:
Jackson State Univ., Jackson, MS (United States)
Sponsoring Org.:
USDOE Office of Science (SC); Government of India; National Institute of Pharmaceutical Education and Research Kolkata (NIPER-Kolkata); University Grants Commission (UGC), New Delhi; National Science Foundation (NSF); Council of Scientific & Industrial Research (CSIR)
OSTI Identifier:
1598518
Alternate Identifier(s):
OSTI ID: 1597533
Grant/Contract Number:  
SC0018322; OIA-1757220
Resource Type:
Accepted Manuscript
Journal Name:
Nano Energy
Additional Journal Information:
Journal Volume: 70; Journal Issue: C; Journal ID: ISSN 2211-2855
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; Chemometrics; DSSC; Dye; PCE; QSPR; Solar cell

Citation Formats

Krishna, Jillella Gopala, Ojha, Probir Kumar, Kar, Supratik, Roy, Kunal, and Leszczynski, Jerzy. Chemometric modeling of power conversion efficiency of organic dyes in dye sensitized solar cells for the future renewable energy. United States: N. p., 2020. Web. doi:10.1016/j.nanoen.2020.104537.
Krishna, Jillella Gopala, Ojha, Probir Kumar, Kar, Supratik, Roy, Kunal, & Leszczynski, Jerzy. Chemometric modeling of power conversion efficiency of organic dyes in dye sensitized solar cells for the future renewable energy. United States. https://doi.org/10.1016/j.nanoen.2020.104537
Krishna, Jillella Gopala, Ojha, Probir Kumar, Kar, Supratik, Roy, Kunal, and Leszczynski, Jerzy. Tue . "Chemometric modeling of power conversion efficiency of organic dyes in dye sensitized solar cells for the future renewable energy". United States. https://doi.org/10.1016/j.nanoen.2020.104537. https://www.osti.gov/servlets/purl/1598518.
@article{osti_1598518,
title = {Chemometric modeling of power conversion efficiency of organic dyes in dye sensitized solar cells for the future renewable energy},
author = {Krishna, Jillella Gopala and Ojha, Probir Kumar and Kar, Supratik and Roy, Kunal and Leszczynski, Jerzy},
abstractNote = {The present study reports chemometric modeling of power conversion efficiency (PCE) of dye sensitized solar cells (DSSCs) using the biggest available data set till date which comprises around 1200 dyes covering 7 chemical classes. To extract the best structural features required for higher PCE, we have developed multiple partial least squares (PLS) quantitative structure-property relationship (QSPR) models for the Triphenylamine, Phenothiazine, Indoline, Porphyrin, Coumarin, Carbazole and Diphenylamine chemical classes using descriptors derived from the best subset selection method followed by selection of best five models in each dataset based on the Mean Absolute Error (MAE) values. The models were validated both internally and externally followed by the consensus predictions employing “Intelligent Consensus Predictor” tool to examine whether the quality of predictions can be improved with the “intelligent” selection of multiple PLS models. The quality of predictions for the respective external sets showed that the consensus models (CM) are better than the individual models (IM) in most of the cases. From the insights of the developed models, we concluded that attributes like a packed structure toward higher conductivity of electrons, auxiliary donor fragment of aromatic tertiary amines, number of thiophenes inducing the bathochromic shift and augmenting the absorption, presence of additional electron donors, enhancement of electron-donating abilities, number of non-aromatic conjugated C(sp2) which helps as conjugation extension units to broaden the absorption and highly conjugated $π$-systems exert positive contributions to the PCE. On the contrary, features negatively contributing to PCE are the followings: fragments which lower the tendency of localized $π–π*$ transition, fragments related to larger volume and surface area of dyes along with hydrophobicity resulting in poor adhesion, fragment RC = N causing dye hydrolysis, steric hindrance for π electronic mobility, fragments enhancing polarity, etc. Finally, the identified features from the best QSPR model of the coumarin dataset was employed in designing of ten more efficient coumarin dyes (predicted %PCE ranging from 8.93 to 10.62) than the existing ones.},
doi = {10.1016/j.nanoen.2020.104537},
journal = {Nano Energy},
number = C,
volume = 70,
place = {United States},
year = {Tue Jan 28 00:00:00 EST 2020},
month = {Tue Jan 28 00:00:00 EST 2020}
}

Journal Article:

Citation Metrics:
Cited by: 24 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Molecular Photovoltaics
journal, May 2000

  • Hagfeldt, Anders; Grätzel, Michael
  • Accounts of Chemical Research, Vol. 33, Issue 5
  • DOI: 10.1021/ar980112j

Dye-Sensitized Solar Cells
journal, November 2010

  • Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng
  • Chemical Reviews, Vol. 110, Issue 11
  • DOI: 10.1021/cr900356p

Dye-Sensitized Solar Cells: Fundamentals and Current Status
journal, November 2018


Fluorene-Based Sensitizers with a Phenothiazine Donor: Effect of Mode of Donor Tethering on the Performance of Dye-Sensitized Solar Cells
journal, January 2015

  • Baheti, Abhishek; Justin Thomas, K. R.; Li, Chun-Ting
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 4
  • DOI: 10.1021/am506149q

Rational Molecular Engineering of Indoline-Based D-A-π-A Organic Sensitizers for Long-Wavelength-Responsive Dye-Sensitized Solar Cells
journal, November 2015

  • Zhang, Weiwei; Wu, Yongzhen; Zhu, Haibo
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 48
  • DOI: 10.1021/acsami.5b08888

Metal-Free Organic Dyes for Dye-Sensitized Solar Cells: From Structure: Property Relationships to Design Rules
journal, March 2009

  • Mishra, Amaresh; Fischer, Markus K. R.; Bäuerle, Peter
  • Angewandte Chemie International Edition, Vol. 48, Issue 14
  • DOI: 10.1002/anie.200804709

Arylamine organic dyes for dye-sensitized solar cells
journal, January 2013

  • Liang, Mao; Chen, Jun
  • Chemical Society Reviews, Vol. 42, Issue 8
  • DOI: 10.1039/c3cs35372a

Chalcogenophene Comonomer Comparison in Small Band Gap Diketopyrrolopyrrole-Based Conjugated Polymers for High-Performing Field-Effect Transistors and Organic Solar Cells
journal, January 2015

  • Ashraf, Raja Shahid; Meager, Iain; Nikolka, Mark
  • Journal of the American Chemical Society, Vol. 137, Issue 3
  • DOI: 10.1021/ja511984q

A Broadly Absorbing Perylene Dye for Solid-State Dye-Sensitized Solar Cells
journal, July 2009

  • Cappel, Ute B.; Karlsson, Martin H.; Pschirer, Neil G.
  • The Journal of Physical Chemistry C, Vol. 113, Issue 33
  • DOI: 10.1021/jp906409q

Ultrafast Electron Injection:  Implications for a Photoelectrochemical Cell Utilizing an Anthocyanin Dye-Sensitized TiO 2 Nanocrystalline Electrode
journal, November 1997

  • Cherepy, Nerine J.; Smestad, Greg P.; Grätzel, Michael
  • The Journal of Physical Chemistry B, Vol. 101, Issue 45
  • DOI: 10.1021/jp972197w

Combined Experimental and DFT-TDDFT Computational Study of Photoelectrochemical Cell Ruthenium Sensitizers
journal, December 2005

  • Nazeeruddin, Mohammad K.; De Angelis, Filippo; Fantacci, Simona
  • Journal of the American Chemical Society, Vol. 127, Issue 48
  • DOI: 10.1021/ja052467l

Structural effect of carbazole-based coadsorbents on the photovoltaic performance of organic dye-sensitized solar cells
journal, January 2013

  • Choi, In Taek; Ju, Myung Jong; Kang, Sung Ho
  • Journal of Materials Chemistry A, Vol. 1, Issue 32
  • DOI: 10.1039/c3ta11508a

13.6% Efficient Organic Dye-Sensitized Solar Cells by Minimizing Energy Losses of the Excited State
journal, March 2019


Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers
journal, February 2014

  • Mathew, Simon; Yella, Aswani; Gao, Peng
  • Nature Chemistry, Vol. 6, Issue 3
  • DOI: 10.1038/nchem.1861

In silico designing of power conversion efficient organic lead dyes for solar cells using todays innovative approaches to assure renewable energy for future
journal, June 2017

  • Kar, Supratik; Roy, Juganta K.; Leszczynski, Jerzy
  • npj Computational Materials, Vol. 3, Issue 1
  • DOI: 10.1038/s41524-017-0025-z

Optoelectronic Properties of C60 and C70 Fullerene Derivatives: Designing and Evaluating Novel Candidates for Efficient P3HT Polymer Solar Cells
journal, July 2019

  • Roy, Juganta K.; Kar, Supratik; Leszczynski, Jerzy
  • Materials, Vol. 12, Issue 14
  • DOI: 10.3390/ma12142282

A quantitative structure-property relationship study of the photovoltaic performance of phenothiazine dyes
journal, March 2015


Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells
journal, January 2015

  • Venkatraman, Vishwesh; Foscato, Marco; Jensen, Vidar R.
  • Journal of Materials Chemistry A, Vol. 3, Issue 18
  • DOI: 10.1039/C5TA00625B

A cascaded QSAR model for efficient prediction of overall power conversion efficiency of all-organic dye-sensitized solar cells
journal, March 2015

  • Li, Hongzhi; Zhong, Ziyan; Li, Lin
  • Journal of Computational Chemistry, Vol. 36, Issue 14
  • DOI: 10.1002/jcc.23886

Electronic Structure and Optical Properties of Designed Photo-Efficient Indoline-Based Dye-Sensitizers with D–A−π–A Framework
journal, January 2019

  • Roy, Juganta K.; Kar, Supratik; Leszczynski, Jerzy
  • The Journal of Physical Chemistry C, Vol. 123, Issue 6
  • DOI: 10.1021/acs.jpcc.8b10708

The dye-sensitized solar cell database
journal, April 2018

  • Venkatraman, Vishwesh; Raju, Rajesh; Oikonomopoulos, Solon P.
  • Journal of Cheminformatics, Vol. 10, Issue 1
  • DOI: 10.1186/s13321-018-0272-0

Mordred: a molecular descriptor calculator
journal, February 2018

  • Moriwaki, Hirotomo; Tian, Yu-Shi; Kawashita, Norihito
  • Journal of Cheminformatics, Vol. 10, Issue 1
  • DOI: 10.1186/s13321-018-0258-y

PaDEL-descriptor: An open source software to calculate molecular descriptors and fingerprints
journal, December 2010

  • Yap, Chun Wei
  • Journal of Computational Chemistry, Vol. 32, Issue 7
  • DOI: 10.1002/jcc.21707

Comparative QSARs for antimalarial endochins: Importance of descriptor-thinning and noise reduction prior to feature selection
journal, December 2011


Consensus QSAR modeling of toxicity of pharmaceuticals to different aquatic organisms: Ranking and prioritization of the DrugBank database compounds
journal, January 2019


Exploring QSPR modeling for adsorption of hazardous synthetic organic chemicals (SOCs) by SWCNTs
journal, August 2019


Be aware of error measures. Further studies on validation of predictive QSAR models
journal, March 2016


On Various Metrics Used for Validation of Predictive QSAR Models with Applications in Virtual Screening and Focused Library Design
journal, July 2011

  • Roy, Kunal; Mitra, Indrani
  • Combinatorial Chemistry & High Throughput Screening, Vol. 14, Issue 6
  • DOI: 10.2174/138620711795767893

Introduction of rm2(rank) metric incorporating rank-order predictions as an additional tool for validation of QSAR/QSPR models
journal, August 2012


Synthesis and applications of new triphenylamine dyes with donor–donor–(bridge)–acceptor structure for organic dye-sensitized solar cells
journal, January 2012

  • Sakong, Chun; Kim, Hae Joong; Kim, Se Hun
  • New Journal of Chemistry, Vol. 36, Issue 10
  • DOI: 10.1039/c2nj40374a

Triphenylamine based dyes for dye sensitized solar cells: A review
journal, January 2016


Synthesis of triphenylamine-based thiophene-(N-aryl)pyrrole-thiophene dyes for dye-sensitized solar cell applications
journal, July 2012


Tuning the Energy Level of Organic Sensitizers for High-Performance Dye-Sensitized Solar Cells
journal, January 2009

  • Xu, Mingfei; Wenger, Sophie; Bala, Hari
  • The Journal of Physical Chemistry C, Vol. 113, Issue 7
  • DOI: 10.1021/jp809319x

Recent advances in phenothiazine-based dyes for dye-sensitized solar cells
journal, August 2016


Interfacial Electron-Transfer Dynamics in Ru(tcterpy)(NCS) 3 -Sensitized TiO 2 Nanocrystalline Solar Cells
journal, December 2002

  • Bauer, Christophe; Boschloo, Gerrit; Mukhtar, Emad
  • The Journal of Physical Chemistry B, Vol. 106, Issue 49
  • DOI: 10.1021/jp0200268

Screening donor groups of organic dyes for dye-sensitized solar cells
journal, January 2015

  • Yang, Zhenqing; Shao, Changjin; Cao, Dapeng
  • RSC Advances, Vol. 5, Issue 29
  • DOI: 10.1039/C4RA17261B

The chemical bonds effect of Amaranthus hybridus L. and Dracaena Angustifolia on TiO2 as photo-sensitizer for dye-sensitized solar Cells (DSSC)
conference, January 2017

  • Ahliha, A. H.; Nurosyid, F.; Supriyanto, A.
  • THE 4TH INTERNATIONAL CONFERENCE ON RESEARCH, IMPLEMENTATION, AND EDUCATION OF MATHEMATICS AND SCIENCE (4TH ICRIEMS): Research and Education for Developing Scientific Attitude in Sciences And Mathematics, AIP Conference Proceedings
  • DOI: 10.1063/1.4995165

The role of sp 2 /sp 3 hybrid carbon regulation in the nonlinear optical properties of graphene oxide materials
journal, January 2017

  • Wang, Shuai; Dong, Yongli; He, Chunying
  • RSC Advances, Vol. 7, Issue 84
  • DOI: 10.1039/C7RA10505C

Donor-Substituted β-Functionalized Porphyrin Dyes on Hierarchically Structured Mesoporous TiO 2 Spheres. Highly Efficient Dye-Sensitized Solar Cells
journal, September 2011

  • Ishida, Masatoshi; Park, Sun Woo; Hwang, Daesub
  • The Journal of Physical Chemistry C, Vol. 115, Issue 39
  • DOI: 10.1021/jp202307b

Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12 Percent Efficiency
journal, November 2011


Effect of end group polarity upon the lower critical solution temperature of poly(2-isopropyl-2-oxazoline)
journal, October 2008

  • Huber, Stephan; Hutter, Naima; Jordan, Rainer
  • Colloid and Polymer Science, Vol. 286, Issue 14-15
  • DOI: 10.1007/s00396-008-1942-7

Enhanced Charge-Collection Efficiencies and Light Scattering in Dye-Sensitized Solar Cells Using Oriented TiO 2 Nanotubes Arrays
journal, January 2007

  • Zhu, Kai; Neale, Nathan R.; Miedaner, Alexander
  • Nano Letters, Vol. 7, Issue 1
  • DOI: 10.1021/nl062000o

Alkyl-Functionalized Organic Dyes for Efficient Molecular Photovoltaics
journal, November 2006

  • Koumura, Nagatoshi; Wang, Zhong-Sheng; Mori, Shogo
  • Journal of the American Chemical Society, Vol. 128, Issue 44
  • DOI: 10.1021/ja0645640

D-π-A Sensitizers for Dye-Sensitized Solar Cells: Linear vs Branched Oligothiophenes
journal, March 2010

  • Fischer, Markus K. R.; Wenger, Sophie; Wang, Mingkui
  • Chemistry of Materials, Vol. 22, Issue 5
  • DOI: 10.1021/cm903542v

Novel D–π–A structured porphyrin dyes with diphenylamine derived electron-donating substituents for highly efficient dye-sensitized solar cells
journal, January 2013

  • Kang, Sung Ho; Choi, In Taek; Kang, Min Soo
  • Journal of Materials Chemistry A, Vol. 1, Issue 12
  • DOI: 10.1039/c3ta01128c

Effect of dye extracting solvents and sensitization time on photovoltaic performance of natural dye sensitized solar cells
journal, January 2017


Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells
journal, January 2014


Use of organic materials in dye-sensitized solar cells
journal, June 2017