4,5-Difluoro-1,2-dehydrobenzene: generation and cycloaddition reactions

Charushin, Valery N.; Kotovskaya, S. K.; Romanova, Svetlana A.; Чупахин, О. Н.; Tomilov, Yury V.; Нефедов, О. М.

doi:10.1070/mc2005v015n02abeh002072

Cited by 15 publications

(9 citation statements)

References 11 publications

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“…The key building block 5,6‐difluoro‐1 H ‐benzotriazole was readily prepared in 75% yield from 5,6‐difluorobenzene‐1,2‐diamine by treatment with sodium nitrite. [ 47 ] Alkylation with the appropriate bromoalkane using Cs 2 CO 3 in dimethylformamide afforded a mixture of the desired product 2‐alkyl‐5,6‐difluorobenzotriazole (dfBTz) and the isomeric 1‐alkyl‐5,6‐difluorobenzotriazole, which required separation by column chromatography. The synthesis of alkylating agents is shown in Scheme S1 (Supporting Information), but we highlight that 11‐(bromomethyl)tricosane (to give 2DT) was readily prepared in one step from the commercial alcohol, whereas 11‐(4‐bromobutyl)tricosane (to give 5DH) required a four‐step synthesis.…”

Section: Resultsmentioning

confidence: 99%

“…The key building block 5,6-difluoro-1H-benzotriazole was readily prepared in 75% yield from 5,6-difluorobenzene-1,2-diamine by treatment with sodium nitrite. [47] Alkylation with the appropriate bromoalkane using Cs 2 CO 3 in dimethylformamide afforded a mixture of the desired product 2-alkyl-5,6-difluorobenzotriazole (dfBTz) Scheme 1. Synthesis of target polymers.…”

Section: Polymer Design and Synthesismentioning

confidence: 99%

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A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

Aniés

Wang

Hodsden

et al. 2020

Adv Elect Materials

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A straightforward synthesis is reported for four structurally simple donor–acceptor conjugated polymers based on an alkylated difluorobenzotriazole and either unsubstituted bithiophene (T2) or thienylvinylthiophene (TVT) co‐monomers. Two solubilizing sidechains are investigated in which the position of the branching point is moved away from the conjugated backbone. Optoelectronic measurements and density functional theory calculations show very similar energetic properties between the polymers, with a slightly narrower bandgap for the vinylene incorporating TVT polymers as a result of extended conjugation. Transistor measurements demonstrate that the simplest polymer, containing a readily available 2‐decyltetradecyl sidechain with a T2 co‐monomer, exhibits the best device performance, with an average saturated mobility of 0.2 cm2 V−1 s−1.

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Section: Resultsmentioning

confidence: 99%

Section: Polymer Design and Synthesismentioning

confidence: 99%

A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

Aniés

Wang

Hodsden

et al. 2020

Adv Elect Materials

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“…The reaction was complete after 4 h. Purification by silica gel flash column chromatography eluting with 30 % ethyl acetate in hexane gave 5,6‐difluoro‐1 H ‐benzo[ d ][1.2.3]triazole ( 2k ) (0.0950 g, 61 %) as an off‐white solid. Mp 176–178 °C (lit . 183–184 °C).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines

et al. 2019

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An operationally simple method has been developed for the preparation of N‐unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2‐aryldiamines under mild conditions, using a polymer‐supported nitrite reagent and p‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N‐alkyl, ‐aryl, and ‐acyl ortho‐aminoanilines leading to the synthesis of N1‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α‐amino acid analogue.

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“…The intermediates and monomers (BTz, BTz-F, BTz-OR) were prepared by modifying the previously reported procedures [15][16][17][18][19][20][21]. 1 H and 13 C NMR spectra were recorded on a JEOL (JNM-AL300) FT NMR system operating at 300 and 75 MHz, respectively.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

Thienothiophene-benzotriazole-based semicrystalline linear copolymers for organic field effect transistors

Yum

Wang

et al. 2014

Pure and Applied Chemistry

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A series of thienothiophene-benzotriazole-based semicrystalline copolymers, PTTBTz, PTTBTz-F, and PTTBTz-OR, were synthesized by considering chain linearity, planarity and inter-chain packing by virtue of non-covalent attractive interaction. Fluorine and alkoxy substituents were introduced to modulate the intra-and inter-chain coulombic interactions and crystalline ordering. The fluorine and alkoxy-substituted PTTBTz-F and PTTBTz-OR showed pronounced inter-chain packing with edge-on orientation confirmed by UV-vis absorption and X-ray diffraction measurements. The well-resolved diffraction patterns were obtained for PTTBTz-F and PTTBTz-OR, showing (100)∼(500) inter-lamellar scattering peaks (d-spacing, 17∼18 Å) in the out-of-plane direction and a π-π stacking peak (d-spacing, 3.5∼4.1 Å) in the in-plane direction. Organic field effect transistor (OFET) devices were fabricated with a bottom gate and top contact geometry. PTTBTz-F (μ h = 4.49 × 10 -2 cm 2 V -1 s -1 , on/off ratio = 1.13 × 10 7 ) and PTTBTz-OR (μ h = 8.39 × 10 -3 cm 2 V -1 s -1 , on/off ratio = 2.98 × 10 4 ) showed nearly 3 and 2 orders of magnitude higher hole mobility upon annealing at 305 and 260 °C, with compared to the unsubstituted PTTBTz.

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4,5-Difluoro-1,2-dehydrobenzene: generation and cycloaddition reactions

Cited by 15 publications

References 11 publications

A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

A Structurally Simple but High‐Performing Donor–Acceptor Polymer for Field‐Effect Transistor Applications

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines

Thienothiophene-benzotriazole-based semicrystalline linear copolymers for organic field effect transistors

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