Planar Heptathienoacenes Based on Unsymmetric Dithieno[3,2-<i>b</i>:3′,4′-d]thiophene: Synthesis and Photophysical Properties

Liu, Qiuxin; Gao, Xiuxiu; Zhong, Hao; Song, Jinsheng; Wang, Hua

doi:10.1021/acs.joc.6b01506

Cited by 9 publications

(12 citation statements)

References 22 publications

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“…The dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) molecular moiety is one of the most promising substructures for thiophene‐based organic semiconductors due to outstanding optoelectronic performances, resulting from remarkable intrinsic molecular properties and possible strong intermolecular interactions . So far, all reported DTT‐containing organic semiconductors exhibit high charge carrier mobility and good environmental stability.…”

Section: Introductionmentioning

confidence: 99%

“…The dithieno[3,2-b;2',3'-d]thiophene (DTT) molecular moiety is one of the most promising substructures for thiophene-based organic semiconductors due to outstanding optoelectronic performances, resulting from remarkable intrinsic molecular properties and possible strong intermolecular interactions. [1][2][3][4] So far, all reported DTT-containing organic semiconductors exhibit high charge carrier mobility and good environmental stability. Such essential features are mainly attributed to the maximization of the π-orbital overlap by restricting or even suppressing intramolecular rotations within the fused ring systems, [5][6][7] and by enhancing the conjugation length through aromatic-coupled structures, causing more rigid and coplanar conformations which facilitate the achievement of closely packed conjugated backbones.…”

Section: Introductionmentioning

confidence: 99%

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Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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Board‐like liquid‐crystalline semiconductors based on the dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) substructure were synthesized and their thermal, self‐assembly, optical, and semiconducting properties investigated. These sanidic compounds, bearing eight peripheral chains, are mesomorphic and spontaneously self‐assemble into columnar hexagonal mesophases (Colhex) over broad temperature ranges, as confirmed by polarized optical microscopy, differential scanning calorimetry, and small‐angle X‐ray scattering. Strong blue photoluminescence with absolute quantum yields up to 33 % were measured. These compounds also form blue‐light emitting gels in various organic solvents. The fibrillar‐like morphology of these gels, reminiscent of the columnar structure, and stabilized by efficient intermolecular interactions, was characterized by scanning electron microscopy. The charge carrier mobility of these π‐extended mesogens was measured by time‐of‐flight transient photocurrent technique in the Colhex mesophase, and showed good hole‐transport performance with charge carrier mobility of 10−3 cm2 V−1 s−1.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Wang

Zhao

et al. 2019

ChemPlusChem

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“…Moreover, the molecular configurations of oligothienoacenes can vary from linear to planar or to helical by changing arrangement of sulfur atoms, especially for [7]thienoacenes (Figure ). , Because of these variable molecular configurations, oligothienoacenes have been widely used as organic functional materials, such as organic light-emitting devices (OLEDs), organic field-effect transistors (OFETs), organic photovoltaic materials (OPVs), and chiral materials …”

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confidence: 99%

From Saddle-Shaped to Planar Cyclic Oligothienoacenes: Stepped-Cyclization and Their Applications in OFETs

Zhao

et al. 2018

Org. Lett.

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A series of cyclic oligothienoacenes (1, 3, and 4) have been successfully synthesized through a stepped-cyclization synthetic strategy from tetra[3,4-thienylene] (2). Single-crystal X-ray diffraction analysis combined with theoretical calculations elucidated that the molecular configuration transforms from the saddle shape of 2 to the quasi-saddle shape (3b, 3c), then to the quasi-helical shape (4b), and at last to the quasi-plane shape (1, 3a, 4a). Organic field-effect transistors (OFETs) based on 1, 3a, and 4a were fabricated. The field-effect mobilities of 7.5 × 10, 2.6 × 10, and 6.8 × 10 cm V s were obtained for 1, 3a, and 4a, respectively. Compounds 3a and 4a can act as air-stable p-type organic semiconductors, while 1 is sensitive to the air.

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“…Aside from [7]helicenes and TTTPs, the intramolecular selective deprotonation of bi-DTTs may generate numerous heptathienoacene isomers. 5,6 These features are useful in both organic synthesis and the development of organic functional materials.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Synthesis of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6trimethylsilanyl-dithieno-[2,3-b:2′,3′-d]thiophene (6). t-BuLi (0.92 mL, 1.2 M in pentane, 1.06 mmol, 2.05 equiv) was added dropwise into a solution of 4 (180 mg, 0.52 mmol, 1.0 equiv) in Et 2 O (25 mL) at −78 °C in a cooling bath.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synthesis of All Thiophene-Based [7]Helicenes and Trithienothiepines with Isomeric Location of Sulfur Atoms Based on Intramolecular Selectivity of Deprotonation

Wang

et al. 2021

J. Org. Chem.

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Three unsymmetric thiophene-based [7]helicenes, namely, endo-exo-UH-1, endo-top-UH-2, and exo-top-UH-3, with different isomeric locations of sulfur atoms in two terminal thiophene rings were efficiently synthesized using dithieno[2,3-b:3′,2′-d]thiophene (bb-DTT), dithieno[2,3-b:2′,3′-d]thiophene (bt-DTT), and dithieno[2,3-b:3′,4′-d]thiophene (bs-DTT) as building blocks via Suzuki cross-coupling and intramolecular cyclization reactions. Aside from these racemic [7]helicenes, two novel heterocyclic isomers, namely, trithienothiepines TTTP-1 and TTTP-2, were simultaneously obtained during the intramolecular cyclization. Two novel deprotonations of bi-DTTs and cyclization for synthesizing target compounds showed high selectivity and efficiently constructed both UHs and TTTPs. X-ray crystallographic analyses revealed that the UHs have typical helical molecular structures. The isomeric location of sulfur atoms in the two terminal thiophene rings in endo-exo-UH-1, endo-top-UH-2, exo-top-UH-3, and TTTP-1 allowed multiple intermolecular interactions, such as S•••S, S•••C, and S•••H interactions, resulting in different crystal-packing patterns. Moreover, the absorption behaviors of these [7]helicenes, TTTP-1, and TTTP-2 were examined and theoretically calculated. Results indicated that the isomeric location of sulfur atoms plays a key role in tuning intramolecular π-electronic conjugation.

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Planar Heptathienoacenes Based on Unsymmetric Dithieno[3,2-b:3′,4′-d]thiophene: Synthesis and Photophysical Properties

Cited by 9 publications

References 22 publications

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

Nonlinear Nonacenes with a Dithienothiophene Substructure: Multifunctional Compounds that Act as Columnar Mesogens, Luminophores, π Gelators, and p‐Type Semiconductors

From Saddle-Shaped to Planar Cyclic Oligothienoacenes: Stepped-Cyclization and Their Applications in OFETs

Synthesis of All Thiophene-Based [7]Helicenes and Trithienothiepines with Isomeric Location of Sulfur Atoms Based on Intramolecular Selectivity of Deprotonation

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