Indacenodithiophene: a promising building block for high performance polymer solar cells

Li, Yongxi; Gu, Minchao; Pan, Zhe; Zhang, Bin; Yang, Xin; Gu, Junwei; Chen, Yu

doi:10.1039/c7ta02562a

Cited by 93 publications

(83 citation statements)

References 122 publications

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“…As shown in Table and described in Section 3.2, a 0.2 eV smaller HOMO‐LUMO gap is found in IDTT than in IDT, which contributes to the better adsorption properties in the IDTT. Our results are consistent with findings in the field of IDT‐based polymer solar cells …”

Section: Resultssupporting

confidence: 92%

“…In one pentacyclic IDT moiety, five aromatic rings fused into a single unit, leading to good coplanar feature and a much extended π‐conjugated system. The IDT moiety has been widely used as a crucial fabricating component to construct narrow bandgap polymers for high‐efficiency polymer photovoltaic materials . Due to the rigid structural feature and good π‐conjugation, the IDT unit has also been considered for use in DSSC dyes.…”

Section: Introductionmentioning

confidence: 99%

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Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

Fan

Zhao

Liu

et al. 2019

Int J of Quantum Chemistry

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Indacenodithiophene (IDT)‐based high‐efficiency photovoltaics have received increasing attention recently. This paper reports a density functional theory investigation of the electronic and optical properties of three IDT‐based organic dyes together with the dye/(TiO2)46 interface. In order to enhance the photoelectric properties of IDT dyes, this paper considers two methods for the structure modification of the experimentally reported dye DPInDT (J. Org. Chem. 2011, 76, 8977): the extension of the conjugation length by dithienothiophene as well as the heteroatom substitution of the bridging atoms by electron‐rich nitrogen atoms. Our calculations show that both methods obviously affect the distributions of the molecular orbitals and notably red shift the absorption peaks of around 20 nm, with the former method demonstrating enhanced light harvesting efficiency. The structure modifications proposed also enhance the emission spectrum properties for IDT‐based organic dyes. The calculated ultrafast injection time of electrons from the excited state of IDT dyes to the (TiO2)46 belongs to the femtosecond order of magnitude, and is ideal for efficient photoelectric conversion process in dye‐sensitized solar cells (DSSCs) applications. The IDT dyes designed in this paper have good electronic and spectroscopic properties. This study is expected to provide useful guidance for the development of novel IDT dyes for applications in DSSCs.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

Fan

Zhao

Liu

et al. 2019

Int J of Quantum Chemistry

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“…Introduction of EWGs at the terminal thienyl units ( Figure a) have been explored in acceptor–donor–acceptor (A–D–A) nonfullerene acceptors (NFAs) for use in organic solar cells. [ 31,32 ] Several reports have also shown that these IDT‐based NFAs display promising performance in thin‐film transistor applications. [ 33,34 ] Alternative attempts have focused upon chemically modifying the core via the introduction of strong EWGs at the 4,9‐bridging positions of the IDT backbone (Figure 1b).…”

Section: Introductionmentioning

confidence: 99%

Core Fluorination Enhances Solubility and Ambient Stability of an IDT‐Based n‐Type Semiconductor in Transistor Devices

Hodsden

Thorley

Panidi

et al. 2020

Adv Funct Materials

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The synthesis of a novel fluorinated n-type small molecule based on an indacenodithiophene core is reported. Fluorination is found to have a significant impact on the physical properties, including a surprisingly dramatic improvement in solubility, in addition to effectively stabilizing the lowest-unoccupied molecular orbital energy (−4.24 eV). Single-crystal analysis and density functional theory calculations indicate the improved solubility can be attributed to backbone torsion resulting from the positioning of the fluorine group in close proximity to the strongly electron-withdrawing dicyanomethylene group. Organic thin-film transistors made via blade coating display high electron mobility (up to 0.49 cm 2 V −1 s −1 ) along with good retention of performance in ambient conditions.

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“…The ladder-type five membered IDT moiety features desirable and easily tunable properties such as an extended π-conjugated system, an optimal balance of electron density and a quaternary bridging carbon atom that ensures planarity and carries different side groups for solubility and film morphology. 1,2 This coplanarity and the low energetic disorder of the electron rich fused ring aromatic structure favors π-electron delocalization and charge transport. 2,8,[13][14][15][16] The attachment of side groups ensures high solubility for processing OPV 17,18 and OFET devices 5,8 from solution.…”

Section: Introductionmentioning

confidence: 99%

Indacenodithiophene Homopolymers via Direct Arylation: Direct Polycondensation versus Polymer Analogous Reaction Pathways

et al. 2019

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Indacenodithiophene (IDT) based materials are emerging high performance conjugated polymers for use in efficient organic photovoltaics and transistors. However, their preparation generally suffers from long reaction sequences and is often accomplished using disadvantageous Stille couplings. Herein, we present detailed synthesis pathways to IDT homopolymers using C-H activation for all C-C coupling steps. Polyketones are first prepared by direct arylation polycondensation (DAP) in quantitative yield and further cyclized polymer analogously. This protocol is suitable for obtaining structurally well-defined IDT homopolymers, provided that the conditions for cyclization are chosen appropriately and that side reactions are suppressed. Moreover, this polymer analogous pathway gives rise to asymmetric side chain patterns, which allows to fine tune physical properties. Alternatively, IDT homopolymers can be obtained via oxidative direct arylation polycondensation of IDT monomers (oxDAP), leading to IDT homopolymers with similar properties but at reduced yield. Detailed characterization by NMR, IR, UV-vis and PL spectroscopy, and thermal properties, is used to guide synthesis and to explain varying field-effect transistor hole mobilities in the range of 10 -6 -10 -3 cm 2 /Vs.

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Indacenodithiophene: a promising building block for high performance polymer solar cells

Abstract: This review surveys recent research advances in the area of IDT-based conjugated materials for photovoltaic applications. The factors affecting the bandgaps, molecular energy levels, film morphologies, as well as the photovoltaic performance of these materials have also been discussed.

Cited by 93 publications

References 122 publications

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

Molecular design of novel indacenodithiophene‐based organic dyes for efficient dye‐sensitized solar cells applications

Core Fluorination Enhances Solubility and Ambient Stability of an IDT‐Based n‐Type Semiconductor in Transistor Devices

Indacenodithiophene Homopolymers via Direct Arylation: Direct Polycondensation versus Polymer Analogous Reaction Pathways

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