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Synthesis of Organic Chromophores for Dye Sensitized Solar Cells.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. (Licheng Sun)
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

 

This thesis deals with development and synthesis of organic chromophores for dye sensitized solar cells. The chromophores are divided into three components; donor, linker and acceptor.

The development of efficient organic chromophores for dye sensitized solar cells starts off with one new organic chromophore, D5. This chromophore consists of a triphenylamine moiety as an electron donor, a conjugated linker with a thiophene moiety and cyanoacrylic acid as an electron acceptor and anchoring group. Alternating the donor, linker or acceptor moieties independently, would give us the tool to tune the HOMO and LUMO energy levels of the chromophores. The following parts of this thesis regard this development strategy.

The contributions to the HOMO and LUMO energy levels were investigated when alternating the linker moiety. Unexpected effects of the solar cell performances when increasing the linker length were revealed, however.

In addition, the effect of an alternative acceptor group, rhodanine-3-acetic acid, in combination with different linker lengths was investigated. The HOMO and LUMO energy level tuning was once again successful. Electron recombination from the semiconductor to the electrolyte is probably the cause of the poor efficiencies obtained for this series of dyes.

Finally, the development of functionalized triphenylamine based donors and the contributions from different substituents to the HOMO and LUMO energy levels and as insulating layers were investigated. This strategy has so far been the most successful in terms of reaching high efficiencies in the solar cell. A top overall efficiency of 7.79 % was achieved.

 

Place, publisher, year, edition, pages
Stockholm: KTH , 2009. , 73 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2009:18
Keyword [en]
Acceptor, chromophore, donor, dye sensitized solar cells, HOMO and LUMO energy level tuning, linker, organic dye.
National Category
Chemical Engineering
Identifiers
URN: urn:nbn:se:kth:diva-10547ISBN: 978-91-7415-328-6 (print)OAI: oai:DiVA.org:kth-10547DiVA: diva2:219044
Public defence
2009-08-28, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100716Available from: 2009-06-12 Created: 2009-05-26 Last updated: 2010-07-16Bibliographically approved
List of papers
1. A novel organic chromophore for dye-sensitized nanostructured solar cells
Open this publication in new window or tab >>A novel organic chromophore for dye-sensitized nanostructured solar cells
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2006 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 21, 2245-2247 p.Article in journal (Refereed) Published
Abstract [en]

A novel and efficient polyene-diphenylaniline dye for dye-sensitized solar cells has been synthesized. The dye has a short synthesis route and is readily adsorbed on TiO2 under a variety of dye-bath conditions. The overall solar-to-energy conversion efficiency is over 5% in the preliminary tests, in comparison with the conventional N719 dye which gives 6% under the same conditions. The dye is designed for future use also in solid state devices, with triarylamine based hole conductors.

Keyword
nanocrystalline tio2 electrodes, charge-transfer, conversion
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-7881 (URN)10.1039/b603002e (DOI)000237715800011 ()2-s2.0-33744465236 (Scopus ID)
Note
QC 20100716Available from: 2008-01-09 Created: 2008-01-09 Last updated: 2017-12-14Bibliographically approved
2. Molecular Engineering of Organic Chromophores for Dye Sensitized Solar Cell Applications
Open this publication in new window or tab >>Molecular Engineering of Organic Chromophores for Dye Sensitized Solar Cell Applications
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2008 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, 6259-6266 p.Article in journal (Refereed) Published
Abstract [en]

Novel unsymmetrical organic sensitizers comprising donor, electron-conducting, and anchoring groups were engineered at a molecular level and synthesized for sensitization of mesoscopic titanium dioxide injection solar cells. The unsymmetrical organic sensitizers 3-(5-(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D5), 3-(5-bis(4-(diphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D7), 5-(4-(bis(4-methoxyphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D9), and 3-(5-bis(4,4'-dimethoxydiphenylamino)styryl)thiophen-2-yl)-2-cyanoacrylic acid (D11) anchored onto TiO2 and were tested in dye-sensitized solar cell with a volatile electrolyte. The monochromatic incident photon-to-current conversion efficiency of these sensitizers is above 80%, and D11-sensitized solar cells yield a short-circuit photocurrent density of 13.90 +/- 0.2 mA/cm(2), an open-circuit voltage of 740 +/- 10 mV, and a fill factor of 0.70 +/- 0.02, corresponding to an overall conversion efficiency of 7.20% under standard AM 1.5 sun light. Detailed investigations of these sensitizers reveal that the long electron lifetime is responsible for differences in observed open-circuit potential of the cell. As an alternative to liquid electrolyte cells, a solid-state organic hole transporter is used in combination with the D9 sensitizer, which exhibited an efficiency of 3.25%. Density functional theory/time-dependent density functional theory calculations have been employed to gain insight into the electronic structure and excited states of the investigated species.

Place, publisher, year, edition, pages
ACS, 2008
Keyword
nanocrystalline tio2, electron-injection, recombination, semiconductor, chromophores, conductor, energies, dynamics, acceptor, model
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-10534 (URN)10.1021/ja800066y (DOI)000255620200032 ()2-s2.0-43249114905 (Scopus ID)
Note
QC 20100716Available from: 2009-05-25 Created: 2009-05-25 Last updated: 2017-12-13Bibliographically approved
3. Tuning the HOMO and LUMO Energy Levels of Organic Chromophores For Dye Sensitized Solar Cells
Open this publication in new window or tab >>Tuning the HOMO and LUMO Energy Levels of Organic Chromophores For Dye Sensitized Solar Cells
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2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, no 72, 9550-9556 p.Article in journal (Refereed) Published
Abstract [en]

A series of organic chromophores have been synthesized in order to approach optimal energy level composition in the TiO2-dye-iodide/triiodide system in the dye-sensitized solar cells. HOMO and LUMO energy level tuning is achieved by varying the conjugation between the triphenylamine donor and the cyanoacetic acid acceptor. This is supported by spectral and electrochemical experiments and TDDFT calculations. These results show that energetic tuning of the chromophores was successful and fulfilled the thermodynamic criteria for dye-sensitized solar cells, electrical losses depending on the size and orientation of the chromophores were observed.

Keyword
high-efficiency, coumarin dyes, tio2, acid, performance, derivatives, design, light
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-7882 (URN)10.1021/jo701592x (DOI)000251313600017 ()
Note
QC 20100716Available from: 2008-01-09 Created: 2008-01-09 Last updated: 2017-12-14Bibliographically approved
4. Rhodanine Dyes for Dye Sensitized Solar Cells: Spectroscopy, Energy Levels and Photovoltaic Performance
Open this publication in new window or tab >>Rhodanine Dyes for Dye Sensitized Solar Cells: Spectroscopy, Energy Levels and Photovoltaic Performance
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2009 (English)In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 11, 133-141 p.Article in journal (Refereed) Published
Abstract [en]

Three new sensitizers for photoelectrochemical solar cells were synthesized consisting of a triphenylamine donor, a rhodanine-3-acetic acid acceptor and a polyene connection. The conjugation length was systematically increased, which resulted in two effects: first, it led to a red-shift of the optical absorption of the dyes, resulting in an improved spectral overlap with the solar spectrum. Secondly, the oxidation potential decreased systematically. The excited state levels were, however, calculated to be nearly stationary. The experimental trends were in excellent agreement with density functional theory (DFT) computations. The photovoltaic performance of this set of dyes as sensitizers in mesoporous TiO2 solar cells was investigated using electrolytes containing the iodide/triiodide redox couple. The dye with the best absorption characteristics showed the poorest solar cell efficiency, due to losses by recombination of electrons in TiO2 with triiodide. Addition of 4-tert butylpyridine to the electrolyte led to a strongly reduced photocurrent for all dyes due to a reduced electron injection efficiency, caused by a 0.15 V negative shift of the TiO2 conduction band potential.

Place, publisher, year, edition, pages
Cambridge: RSC Publishing, 2009
Keyword
Solar Cells
National Category
Chemical Sciences
Identifiers
urn:nbn:se:kth:diva-10529 (URN)10.1039/b812154k (DOI)000263278900011 ()2-s2.0-57449121558 (Scopus ID)
Note

QC 20150724

Available from: 2009-05-25 Created: 2009-05-25 Last updated: 2017-12-13Bibliographically approved
5. A Light Resistant Organic Sensitizer for Solar Cell Applications
Open this publication in new window or tab >>A Light Resistant Organic Sensitizer for Solar Cell Applications
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2009 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, 1576-1580 p.Article in journal (Refereed) Published
Abstract [en]

(Figure Presented) Finely tuned: A stable dye-sensitized solar cell that contains a molecularly engineered organic dye has been prepared. The efficiency of the cell remains at 90% after 1000 h of light soaking at 60 °C. The remarkable stability of the cell is also reflected in the open-circuit voltage value (Voc), short-circuit photocurrent-density value (J sc), and the fill factor, which also show barely no decline (see picture).

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH & Co., 2009
Keyword
dyes/pigments; electrochemistry; long-term stability; sensitizers; solar cells
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-10536 (URN)10.1002/anie.200804719 (DOI)000263642300008 ()2-s2.0-60749123439 (Scopus ID)
Note
QC 20100716Available from: 2009-05-25 Created: 2009-05-25 Last updated: 2017-12-13Bibliographically approved
6. Highly efficient Organic Sensitizers for Solid State Dye Sensitized Solar Cells
Open this publication in new window or tab >>Highly efficient Organic Sensitizers for Solid State Dye Sensitized Solar Cells
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2009 (English)In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 113, no 38, 16816-16820 p.Article in journal (Refereed) Published
Abstract [en]

Organic sensitizers comprising of donor, electron-conducting, and anchoring groups designed and developed for dye-sensitized solar cell applications. The solar cell employing a spiro-OMeTAD hole transporting material exhibits a short circuit photocurrent density of 9.64 mA/cm2, the open circuit voltage of 798 mV and a fill factor of 0.57, corresponding to an overall conversion efficiency of 4.4% at standard AM 1.5 sunlight. Photo-induced absorption spectroscopy probes an efficient hole-transfer from dyes to the spiro-OMeTAD.

Keyword
PHOTOINDUCED ABSORPTION-SPECTROSCOPY; TIO2; CONVERSION
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-10545 (URN)10.1021/jp9033722 (DOI)000269745700037 ()2-s2.0-70349880505 (Scopus ID)
Note
Uppdaterad från manuskrift 20100716 QC 20100716Available from: 2009-05-26 Created: 2009-05-26 Last updated: 2017-12-13Bibliographically approved
7. Symmetric and Unsymmetric Donor Functionalization. Comparing Structural and Spectral Benefits of Chromophores for Dye Sensitized Solar Cells.
Open this publication in new window or tab >>Symmetric and Unsymmetric Donor Functionalization. Comparing Structural and Spectral Benefits of Chromophores for Dye Sensitized Solar Cells.
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2009 (English)In: Journal of Materials Chemistry, ISSN 0959-9428, E-ISSN 1364-5501, Vol. 19, 7232-7238 p.Article in journal (Refereed) Published
Abstract [en]

 

A series of organic chromophores have been synthesized in order to investigate the benefits of structural versus spectral properties as well as the absorption properties and solar cell performance when introducing unsymmetrical substituents in the chromophore. Exceptionally high Voc was found for the symmetrical, structural benefited dye, which also gave the best overall solar cell performance.

 

Keyword
EFFICIENT MOLECULAR PHOTOVOLTAICS; NANOCRYSTALLINE TIO2 ELECTRODES; ORGANIC-DYES; HIGHLY EFFICIENT; PERFORMANCE; CONVERSION; DESIGN; LIGHT; DERIVATIVES; ACID
National Category
Chemical Engineering
Identifiers
urn:nbn:se:kth:diva-10546 (URN)10.1039/b911397p (DOI)000270382400011 ()2-s2.0-70349789520 (Scopus ID)
Note
QC 20100716Available from: 2009-05-26 Created: 2009-05-26 Last updated: 2017-12-13Bibliographically approved

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