Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Su, Feng; Chen, Shuqi; Mo, Xiaogang; Wu, Kongchuan; Wu, J. F.; Lin, Whei-Min; Lin, Zhi-Wei; Lin, Jianbin; Zhang, Hui‐Jun; Wen, Ting Bin

doi:10.1039/c9sc05332h

Cited by 30 publications

(26 citation statements)

References 55 publications

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“…1a ). The rigidity of the π-skeleton can be further enhanced via the hydrogen bonds 32 and chalcogen bonds 33 . The incorporation of heteroatoms in helicenes would offer the possibility to tune their band gap.…”

Section: Resultsmentioning

confidence: 99%

π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

et al. 2021

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Despite great challenges, the development of new molecular structures with multiple and even conflicting characteristics are eagerly pursued for exploring advanced applications. To develop high-performance chiral organic semiconducting molecules, a distorted π-system is required for strong coupling with circularly polarized light (CPL), whereas planar π-stacking systems are necessary for high charge-carrier mobility. To address this dilemma, in this work, we introduce a skeleton merging approach through distortion of a perylene diimide (PDI) core with four fused heteroaromatics to form an ortho-π-extended PDI double-[7]heterohelicene. PDI double helicene inherits a high dissymmetry factor from the helicene skeleton, and the extended π-planar system concurrently maintains a high level of charge transport properties. In addition, ortho-π-extension of the PDI skeleton brings about near-infrared (NIR) light absorption and ambipolar charge transport abilities, endowing the corresponding organic phototransistors with high photoresponsivity of 450 and 120 mA W−1 in p- and n-type modes respectively, along with a high external quantum efficiency (89%) under NIR light irradiations. Remarkably, these multiple characteristics enable high-performance broadband CPL detections up to NIR spectral region with chiral organic semiconductors.

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Section: Resultsmentioning

confidence: 99%

π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

et al. 2021

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“…Naphthylphenylacetylene 71 reacted with sulfur at rt with NaOH as a base in DMF to provide fused thiophene 72 in low yield along with its dimer disulfide 73 (Scheme 27). [28] When the reaction was performed at higher temperature with NEt 3 as a base, the reaction resulted in thiophene 72 in excellent yield.…”

Section: Scheme 19mentioning

confidence: 99%

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Nguyen

2020

Adv Synth Catal

145

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“…Synthesis and Isolation. Scheme 2depicts our synthesis of [4]C-NDTIs.T he key building block 2,6-bis(trimethylsilyl)-NDTI (1)w as readily synthesized by oxidative cyclization of 2,6-bis(trimethylsilyl)ethynyl-NDI with K 2 S. [20,25] NDTI unit 1 was then converted into 2,6-bis(trimethyltin)-NDTI (3)v ia successive iodination and stannylation in high yields.T rans-metalation of [Pt(COD)Cl 2 ]with 3 was performed at 45 8 8Cin THF for 2days.B ecause pure tetranuclear Pt-complex 4 is not stable during the isolation, the resulting complex mixture was directly subjected to the ligand exchange and reductive elimination reactions.T reatment of 4 with excess triphenylphosphine (PPh 3 ) [9a] or 1,1'-bis(diphenylphosphino)ferrocene (dppf) only afforded the corresponding binuclear platinum complex 5aor 5b.Their structures were established by singlecrystal X-ray diffraction analysis (Figure S1, CCDC 2087509, 2098014). Thermally activated reductive eliminations from 5 were impeded because of the strong bonds between Pt and NDTI ligand and high ring strain energy of [4]C-NDTIs.…”

Section: Resultsmentioning

confidence: 99%

Naphthodithiophene Diimide Based Chiral π‐Conjugated Nanopillar Molecules

Zhang

et al. 2021

Angewandte Chemie

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The synthesis,structures,and properties of [4]cyclonaphthodithiophene diimides ([4]C-NDTIs) are described. NDTIs as important n-type building blocks were catenated in the a-positions of thiophene rings via an unusual electrochemical-oxidation-promoted macrocyclization route.T he thiophene-thiophene junction in [4]C-NDTIs results in an ideal pillar shape.T his interesting topology,a long with appealing electronic and optical properties inherited from the NDTI units,e ndows the [4]C-NDTIs with both near-infrared (NIR) light absorptions,s trong excitonic coupling,a nd tight encapsulation of C 60 .S table orientations of the NDTI units in the nanopillars lead to stable inherent chirality,w hiche nables detailed circular dichroism studies on the impact of isomeric structures on p-conjugation. Remarkably,t he [4]C-NDTIs maintain the strong p-p stacking abilities of NDTI units and thus adopt two-dimensional (2D) lattice arrays at the molecular level. These nanopillar molecules have great potential to mimic natural photosynthetic systems for the development of multifunctional organic materials.

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Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Abstract: A facile stitching thienannulation between acetylenic rylene dyes and S3˙− for rapid synthesis of largely π-extended thienoacenes was developed.

Cited by 30 publications

References 55 publications

π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Naphthodithiophene Diimide Based Chiral π‐Conjugated Nanopillar Molecules

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