A p-π* conjugated triarylborane as an alcohol-processable n-type semiconductor for organic optoelectronic devices

Yu, Yingjian; Dong, Changshuai; Alahmadi, Abdullah F.; Meng, Bin; Li, Jun; Jäkle, Frieder; Wang, Lixiang

doi:10.1039/c9tc01562k

Cited by 42 publications

(27 citation statements)

References 86 publications

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“…This has led to the generation of several boron‐containing functional materials, including boron‐containing conjugated polymers [4a, 5] . For example, conjugated polymers containing FBDT units were prepared that showed n‐type semiconducting properties and photovoltaic applications in bulk heterojunction polymer solar cells [5c, 6] …”

Section: Introductionmentioning

confidence: 99%

Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units

Adachi

Nabeya

Kawakami

et al. 2021

Chemistry A European J

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The introduction of unconventional elements into π‐conjugated systems has been studied to manipulate the electronic states and properties of compounds. Herein, boron‐ and germanium‐containing hybrid macrocycles, as a new class of element‐hybrid conjugated systems, have been synthesized. The palladium‐catalyzed Stille cross coupling of bis(bromothienyl)borane and bis(trimethylstannylthienyl)‐ or bis(trimethylstannylphenyl)‐substituted dithienogermoles as the boron‐ and germanium‐containing building blocks, respectively, produced a mixture of several macrocyclic compounds. Single‐crystal X‐ray analysis of the 2:2 coupling product revealed a planar structure with a cavity inside the macrocycle. The optical properties of the macrocyclic products indicated rather small electronic interactions between the building units. However, intramolecular photoenergy transfer from the dithienogermole unit to the boron unit was clearly observed with respect to the fluorescence spectra.

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Section: Introductionmentioning

confidence: 99%

Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units

Adachi

Nabeya

Kawakami

et al. 2021

Chemistry A European J

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“…Herein, we designed and synthesized a series of DPP‐based n‐type polymer semiconductors BTIn‐DPP ( n = 1, 2, 3, Figure c) by introducing distinct BTIn into polymer backbone. The incorporation of these ladder‐type BTIn units yields polymers with narrow band gap (≈1.3 eV) and also effectively downshifts their LUMO energy levels to approximately −3.4 eV, thus leading to n‐type characteristic in OTFT devices . Specifically, a highest µ e up to 0.48 cm 2 V −1 s −1 was achieved for the BTI2‐DPP polymer (Figure b) due to its high degree of backbone planarity and film crystallinity.…”

Section: Molecular Weights and Optical And Electrochemical Propertiementioning

confidence: 99%

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Zhang

Tang

Sun

et al. 2019

Macromol. Rapid Commun.

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Polymer semiconductors have drawn much attention from both academia and industry due to their unique advantages for the fabrication of light-weight, largearea, low-cost, and flexible/stretchable electronic devices, such as organic thinfilm transistors (OTFTs) and organic solar cells (OSCs). [1][2][3][4][5][6][7][8][9] Recently, OTFTs have achieved promising device performance with charge carrier mobility exceeding that (0.1-1 cm 2 V −1 s −1 ) of amorphous silicon-based transistors. However, most of high-performance polymers exhibit p-type predominant or ambipolar transport characteristic in OTFT devices to date. [10][11][12][13][14][15] Due to the synthetic challenge and associated steric hindrance of highly electron-deficient building blocks, which are essential for n-type semiconductors, the development of n-type polymers far lagged behind the p-type or ambipolar analogues. [10,[16][17][18] Hence, in order to realize applications such as complementary metal-oxide-semiconductor (CMOS)-like logic circuits and all-polymer solar cells, [18][19][20] it is highly urgent to design and synthesize high-performance n-type polymer semiconductors with comparable device performance characteristics, such as charge carrier mobility and device stability.Benefiting from high electron deficiency, coplanar backbone conformation, and easy access, diketopyrrolo[3,4-c]pyrrole (DPP) is regarded as a remarkable electron-accepting building block and has been widely applied for constructing donor-acceptor (D-A) polymer semiconductors in the past decade, showing substantial charge carrier mobility in OTFT devices. [10,16,[21][22][23] The highest OTFT mobility based on DPP-incorporated polymer semiconductors has now surpassed 10 cm 2 V −1 s −1 (Figure 1a). [24] However, the electron-rich nature of the flanking thiophene moieties in DPP showed negative effects on the optimization of frontier molecular orbital (FMO) energy levels for n-type performance, resulting in a p-type dominating or ambipolar transport characteristic for most of the DPP-based copolymers (Figure 1a). [25][26][27] In this regard, copolymerizing DPP with another strong electron-acceptor co-unit should be an effective strategy for downshifting FMO energy levels, which is hence beneficial for achieving improved n-type performance due to Diketopyrrolopyrrole (DPP)-based copolymers have received considerable attention as promising semiconducting materials for high-performance organic thin-film transistors (OTFTs). However, these polymers typically exhibit p-type or ambipolar charge-transporting characteristics in OTFTs due to their high-lying highest occupied molecular orbital (HOMO) energy levels. In this work, a new series of DPP-based n-type polymers have been developed by incorporating fused bithiophene imide oligomers (BTIn) into DPP polymers. The resulting copolymers BTIn-DPP show narrow band gaps as low as 1.27 eV and gradually down-shifted frontier molecular orbital energy levels upon the increment of imide group number. Benefiting from the coplanar backbone conforma...

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“…10,11 Among all electron-accepting chromophores, boron(III)-containing moieties are anticipated to be promising candidates due to the vacant p-orbital on the boron center, making them inherently electron decient. [12][13][14] To date, a number of molecular NFAs using three-coordinate boranes or four-coordinate borates as electron-accepting chromophores for solutionprocessable OSCs have been reported in the literature; [15][16][17][18][19][20][21][22] however, only those NFAs containing double B ) N bridged bipyridine-based four-coordinate borates show PCEs exceeding 4%. 21,22 On the other hand, air-stable boron(III) b-diketonates, a family of classical four-coordinate borates, have proven to show strong luminescence, large extinction coefficients and nonlinear optical properties.…”

Section: Introductionmentioning

confidence: 99%

Boron(iii) β-diketonate-based small molecules for functional non-fullerene polymer solar cells and organic resistive memory devices

Liang

Hong

et al. 2020

Chem. Sci.

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A p-π* conjugated triarylborane as an alcohol-processable n-type semiconductor for organic optoelectronic devices

Cited by 42 publications

References 86 publications

Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units

Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units

Fused Bithiophene Imide Oligomer and Diketopyrrolopyrrole Copolymers for n‐Type Thin‐Film Transistors

Boron(iii) β-diketonate-based small molecules for functional non-fullerene polymer solar cells and organic resistive memory devices

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