Molecular engineering and synthesis of symmetric metal-free organic sensitizers with A-π-D-π-A architecture for DSSC applications: the effect of bridge unit
Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers ( llyu1a, llyu1b, llyu1c, llyu2a, llyu2b, and llyu2c ) based on fluorene or dimethyl fluorene donors core carrying double acceptors. All these dyes were characterized using UV–Vis, ESI-MS, and 1 HNMR. To study...
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Published in | Journal of the Iranian Chemical Society Vol. 16; no. 11; pp. 2441 - 2450 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Berlin/Heidelberg
Springer Berlin Heidelberg
01.11.2019
Springer Nature B.V |
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Abstract | Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (
llyu1a, llyu1b, llyu1c, llyu2a, llyu2b,
and
llyu2c
) based on fluorene or dimethyl fluorene donors core carrying double acceptors. All these dyes were characterized using UV–Vis, ESI-MS, and
1
HNMR. To study the influence of π-bridges on total solar-to-electric conversion efficiency (%
η
) for DSSCs, three different π-bridges thiophene, furane, or benzene were introduced into the sensitizers. Their device performances were studied and showed a distinctive difference in efficiency with a maximum of PCE of 2.35% (
Jsc
= 5.63 mA cm − 2,
V
OC
= 0.60 V and
FF
= 70.00%) for dye
llyu1a
. Density functional theory (DFT) and time-dependent density functional theory calculations were used to probe the relationship between chemical structure, photophysical, and photoelectrochemical properties. DFT studies showed that the dihedral angle between thiophene and donor is 26.6°, indicating that the dyes bearing thiophene π-bridge possess more efficient photoexcitation compared to dyes bearing benzene π-bridge (36.6° for both
llyu2c
and
llyu1c
) and less aggregation than dyes bearing furane π-bridge (0° for
llyu1b
and
llyu2b
). This new finding of influence of π-bridges on total solar-to-electric conversion efficiency would open the door for the molecular engineering of better light harvesting and more efficient metal-free organic sensitizers for DSSCs. |
---|---|
AbstractList | Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (
llyu1a, llyu1b, llyu1c, llyu2a, llyu2b,
and
llyu2c
) based on fluorene or dimethyl fluorene donors core carrying double acceptors. All these dyes were characterized using UV–Vis, ESI-MS, and
1
HNMR. To study the influence of π-bridges on total solar-to-electric conversion efficiency (%
η
) for DSSCs, three different π-bridges thiophene, furane, or benzene were introduced into the sensitizers. Their device performances were studied and showed a distinctive difference in efficiency with a maximum of PCE of 2.35% (
Jsc
= 5.63 mA cm − 2,
V
OC
= 0.60 V and
FF
= 70.00%) for dye
llyu1a
. Density functional theory (DFT) and time-dependent density functional theory calculations were used to probe the relationship between chemical structure, photophysical, and photoelectrochemical properties. DFT studies showed that the dihedral angle between thiophene and donor is 26.6°, indicating that the dyes bearing thiophene π-bridge possess more efficient photoexcitation compared to dyes bearing benzene π-bridge (36.6° for both
llyu2c
and
llyu1c
) and less aggregation than dyes bearing furane π-bridge (0° for
llyu1b
and
llyu2b
). This new finding of influence of π-bridges on total solar-to-electric conversion efficiency would open the door for the molecular engineering of better light harvesting and more efficient metal-free organic sensitizers for DSSCs. Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (llyu1a, llyu1b, llyu1c, llyu2a, llyu2b, and llyu2c) based on fluorene or dimethyl fluorene donors core carrying double acceptors. All these dyes were characterized using UV–Vis, ESI-MS, and 1HNMR. To study the influence of π-bridges on total solar-to-electric conversion efficiency (%η) for DSSCs, three different π-bridges thiophene, furane, or benzene were introduced into the sensitizers. Their device performances were studied and showed a distinctive difference in efficiency with a maximum of PCE of 2.35% (Jsc = 5.63 mA cm − 2, VOC = 0.60 V and FF = 70.00%) for dye llyu1a. Density functional theory (DFT) and time-dependent density functional theory calculations were used to probe the relationship between chemical structure, photophysical, and photoelectrochemical properties. DFT studies showed that the dihedral angle between thiophene and donor is 26.6°, indicating that the dyes bearing thiophene π-bridge possess more efficient photoexcitation compared to dyes bearing benzene π-bridge (36.6° for both llyu2c and llyu1c) and less aggregation than dyes bearing furane π-bridge (0° for llyu1b and llyu2b). This new finding of influence of π-bridges on total solar-to-electric conversion efficiency would open the door for the molecular engineering of better light harvesting and more efficient metal-free organic sensitizers for DSSCs. |
Author | Han, Liang Tang, Ping Lyu, Luping Tong, Guotong |
Author_xml | – sequence: 1 givenname: Luping surname: Lyu fullname: Lyu, Luping email: mailofllp@126.com organization: Linjiang College, Hangzhou Vocational and Technical College – sequence: 2 givenname: Ping surname: Tang fullname: Tang, Ping organization: Linjiang College, Hangzhou Vocational and Technical College – sequence: 3 givenname: Guotong surname: Tong fullname: Tong, Guotong organization: Linjiang College, Hangzhou Vocational and Technical College – sequence: 4 givenname: Liang surname: Han fullname: Han, Liang organization: College of Chemical Engineering, Zhejiang University of Technology |
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Keywords | Double π-acceptors DSSCs Fluorene Symmetric organic dyes |
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Snippet | Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (
llyu1a, llyu1b, llyu1c, llyu2a, llyu2b,
and
llyu2c
) based on... Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (llyu1a, llyu1b, llyu1c, llyu2a, llyu2b, and llyu2c) based on... |
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SubjectTerms | Analytical Chemistry Bearing Benzene Biochemistry Bridges Chemical synthesis Chemistry Chemistry and Materials Science Conversion Density functional theory Dihedral angle Dyes Efficiency Electric bridges Hydrocarbons Inorganic Chemistry Organic Chemistry Original Paper Photoexcitation Photovoltaic cells Physical Chemistry Time dependence |
Title | Molecular engineering and synthesis of symmetric metal-free organic sensitizers with A-π-D-π-A architecture for DSSC applications: the effect of bridge unit |
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