Visible and Near-Infrared Absorbing, Low Band Gap Conjugated Oligomers Based on Cyclopentadieneones

Walker, Wesley; Veldman, Brittnee; Chiechi, Ryan C.; Patil, Satish; Bendikov, Michael; Wudl, Fred

doi:10.1021/ma8004873

Cited by 41 publications

(34 citation statements)

References 31 publications

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“…Recently, there has been a considerable interest in low bandgap conjugated polymers, specifically those with bandgaps below 1.5 eV 1. Such materials can provide unique electronic and optical properties, such as near‐infrared (NIR) absorption, NIR emission, and solid‐state charge transport 2.…”

Section: Introductionmentioning

confidence: 99%

Low bandgap π‐conjugated copolymers based on fused thiophenes and benzothiadiazole: Synthesis and structure‐property relationship study

Zhang¹,

Guo²,

Fan³

et al. 2009

J. Polym. Sci. A Polym. Chem.

103

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A series of low bandgap conjugated polymers consisting of benzothiadiazole alternating with dithienothiophene (DTT) or dithienopyrrole (DTP) unit with or without 3-alkylthiophene bridge have been synthesized. Effect of the fused rings and 3-alkylthiophene bridge on the thermal, optical, electrochemical, charge transport, and photovoltaic properties of these polymers have been investigated. These polymers show broad absorption extending from 300 to 1000 nm with optical bandgaps as low as 1.2 eV; the details of which can be varied either by incorporating 3-alkylthiophene bridge or by replacing DTT with DTP. The LUMO levels (À2.9 to À3.3 eV) are essentially unaffected by the specific choice of donor moiety, whereas the HOMO levels (À4.6 to À5.6 eV) are more sensitive to the choice of donor. The DTT and DTP polymers with 3-alkylthiophene bridge were found to exhibit hole mobilities of 8 Â 10 À5 and 3 Â 10 À2 cm 2 V À1 s À1 , respectively, in top-contact organic field-effect transistors. Power conversion efficiencies in the range 0.17-0.43% were obtained under simulated AM 1.5, 100 mW cm À2 irradiation for polymer solar cells using the DTT and DTP-based polymers with 3-alkylthiophene bridge as donor and fullerene derivatives as acceptor.

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Section: Introductionmentioning

confidence: 99%

Low bandgap π‐conjugated copolymers based on fused thiophenes and benzothiadiazole: Synthesis and structure‐property relationship study

Zhang¹,

Guo²,

Fan³

et al. 2009

J. Polym. Sci. A Polym. Chem.

103

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“…[19][20][21][22][23][24][25][26] To create a push-pull system, we have recently prepared a series of polymers based on diaryl-dithienylcyclopentadienone (2,5-dithienyl-3,4-(1,8-naphthylene)cyclopentadienone, DTCPD), revealing a broad absorption band covering practically the whole visible region. 27,28 Given the attractive properties of DTCPD and those of the regioregular thiophene-based materials, we have combined the two units into a new polymer repeat unit. Following the ICT strategy, 4,4′-dialkyl-[2,2′]bithiophene (DAT) moieties are selected as an electron-rich comonomer for DTCPD since tail-to-tail regiopositioning of the alkyl chains on the thiophene monomer helps promote self-organization, while minimizing any steric interactions between neighboring alkyl groups, thus preserving backbone planarity.…”

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confidence: 99%

“…First, 2,5-dithienyl-3,4-(1,8-naphthylene)cyclopentadienone (DTCPD) was prepared by procedures described earlier (DCC-mediated and double Knoevenagel condensation). 27,28 The desired 2,5-di(5-bromothienyl)-3,4-(1,8-naphthylene)cyclopentadienone (1) was obtained after treatment with bromine in acetic acid/ dichloromethane (95% 32 were converted to the corresponding distannyl comonomers via dilithiation and subsequent reaction with trimethylstannyl chloride. 33 The DTCPD units were incorporated with the DAT comonomer into the polymer backbone via palladium(0)-mediated Stille-type polycondensation, affording a series of DTCPD-alt-DAT copolymers (DTCPD-alt-DHT and DTCPD-alt-DDT).…”

mentioning

confidence: 99%

Visible−Near Infrared Absorbing Dithienylcyclopentadienone−Thiophene Copolymers for Organic Thin-Film Transistors

et al. 2008

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Solution-processable organic semiconductors with relatively highmobility are required for printing low-cost organic thin-film transistor (OTFT) circuits for flexible electronics. 1-6 Thiophenebased conjugated polymers have been extensively studied as materials for such applications. 7-10 In particular, as a result of the structural regularity of the polymer backbone, regioregular poly(3-hexylthiophene) (rr-P3HT) exhibits a relatively high charge-carrier (hole) mobility. 11,12 Another important development in the synthesis of π-conjugated polymers has been the utilization of donor-acceptor architectures within the backbone. The donor-acceptor systems cause partial intramolecular charge transfer (ICT) that enables manipulation of the electronic structure (HOMO/LUMO levels), leading to low band gap semiconducting polymers 13-18 with relatively high charge carrier mobilities. [19][20][21][22][23][24][25][26] To create a push-pull system, we have recently prepared a series of polymers based on diaryl-dithienylcyclopentadienone (2,5-dithienyl-3,4-(1,8-naphthylene)cyclopentadienone, DTCPD), revealing a broad absorption band covering practically the whole visible region. 27,28 Given the attractive properties of DTCPD and those of the regioregular thiophene-based materials, we have combined the two units into a new polymer repeat unit. Following the ICT strategy, 4,4′-dialkyl-[2,2′]bithiophene (DAT) moieties are selected as an electron-rich comonomer for DTCPD since tail-to-tail regiopositioning of the alkyl chains on the thiophene monomer helps promote self-organization, while minimizing any steric interactions between neighboring alkyl groups, thus preserving backbone planarity. 29 Besides, it is expected that the unsubstituted thiophene units in DTCPD can increase the ionization potential (IP) via improving rotational freedom, 30,31 possibly resulting in enhanced oxidative stability when compared to that of the poly(alkylthiophene)s.Herein, we present the synthesis of a series of alternating DTCPD-DAT copolymers (DTCPD-alt-DHT and DTCPD-alt-DDT) and the initial characterization of these copolymers. We report the first examples of the performance of organic field-effect transistors (OFETs) fabricated from DTCPD-based copolymers (Figure 1).The synthesis of the donor-acceptor copolymers is depicted in Scheme 1. First, 2,5-dithienyl-3,4-(1,8-naphthylene)cyclopentadienone (DTCPD) was prepared by procedures described earlier (DCC-mediated and double Knoevenagel condensation). 27,28 The desired 2,5-di(5-bromothienyl)-3,4-(1,8-naphthylene)cyclopentadienone (1) was obtained after treatment with bromine in acetic acid/ dichloromethane (95%). 4,4′-Dialkyl[2,2′]bithiophenes (DAT; 4,4′-dihexyl[2,2′]bithiophene (DHT) and 4,4′-didodecyl[2,2′]bithiophenes (DDT)) 32 were converted to the corresponding distannyl comonomers via dilithiation and subsequent reaction with trimethylstannyl chloride. 33 The DTCPD units were incorporated with the DAT comonomer into the polymer backbone via palladium(0)-mediated Stille-type polycondensation, af...

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“…The absence of any photocurrent in response to absorption in the low energy feature centered at 797 nm is similar to the results obtained from DTCPD-alt-DAT copolymers. 23 In addition, it is likely that the ketone part on the backbone of the copolymer becomes an electron trap site and affects the charge transport along the backbone. 27 This puzzling discrepancy implies independent and localized cyclopentadienone moieties.…”

Section: Resultsmentioning

confidence: 99%

“…23 The synthesis of the electron donor moiety (CB) and the succedent polymerization of 9-(5-(9-(heptadecan-9-yl)-9H-carbazol-2-yl)thiophen-2-yl)-3-(4-(nonan-3-yl)phenyl)-7-(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one (DTCPD-alt-CB) copolymer are described in Scheme 1 and Scheme 2, respectively. 23 The synthesis of the electron donor moiety (CB) and the succedent polymerization of 9-(5-(9-(heptadecan-9-yl)-9H-carbazol-2-yl)thiophen-2-yl)-3-(4-(nonan-3-yl)phenyl)-7-(thiophen-2-yl)-8H-cyclopenta[a]acenaphthylen-8-one (DTCPD-alt-CB) copolymer are described in Scheme 1 and Scheme 2, respectively.…”

Section: Synthesismentioning

confidence: 99%

Amorphous dithenylcyclopentadienone-carbazole copolymer for organic thin-film transistors

et al. 2010

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We developed a new high performance amorphous donor-acceptor conjugated copolymer consisting of a dithienylcylclopentadienone subunit as an electron acceptor and carbazole derivative as an electron donor. X-Ray diffraction analysis shows no scattering patterns, indicating that a disordered amorphous solid is formed. Atomic force microscopy (AFM) images show an amorphous surface mophology regardless of the annealing temperature. A high on/off current ratio of approximately 10 6 and high field effect mobility of 2.2 Â 10 À2 cm 2 V À1 s À1 were obtained with stable output characteristics. The high performance of the amorphous copolymer is ascribed to the relatively low activation energy and low characteristic temperature obtained from a low temperature transport analysis, reflecting that localization of the charge carrier is not substantial in the film.

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Visible and Near-Infrared Absorbing, Low Band Gap Conjugated Oligomers Based on Cyclopentadieneones

Cited by 41 publications

References 31 publications

Low bandgap π‐conjugated copolymers based on fused thiophenes and benzothiadiazole: Synthesis and structure‐property relationship study

Low bandgap π‐conjugated copolymers based on fused thiophenes and benzothiadiazole: Synthesis and structure‐property relationship study

Visible−Near Infrared Absorbing Dithienylcyclopentadienone−Thiophene Copolymers for Organic Thin-Film Transistors

Amorphous dithenylcyclopentadienone-carbazole copolymer for organic thin-film transistors

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