Programmed Sequential Additions to Halogenated Mucononitriles

Zahara, Adam; Hinds, Elsa M; Nguyen, Andrew; Wilkerson-Hill, Sidney M.

doi:10.1021/acs.orglett.0c03007

Cited by 11 publications

(8 citation statements)

References 42 publications

(46 reference statements)

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“…Starting from the lowcost raw material of 4, 7-dibromobenzo[c][1,2,5]thiadiazole (1), we successfully synthesized CNDE-Br following the reported two-step procedure. [21] This involved the reduction 4) are first brominated with Br 2 in HOAc at 60 °C overnight. [22] The 3, 4diaminobenzonitrile (5) and 4, 5-diaminophthalonitrile (7) underwent oxidative bromination with KBr, HBr, and tertbutyl hydroperoxide in CH 3 OH for 48 h to afford the intermediates 8 and 10.…”

Section: Resultsmentioning

confidence: 99%

Semiconducting Polymers Based on Simple Electron‐Deficient Cyanated trans‐1,3‐Butadienes for Organic Field‐Effect Transistors

Chen

Wang

et al. 2023

Angew Chem Int Ed

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Developing high‐performance but low‐cost n‐type polymers remains a significant challenge in the commercialization of organic field‐effect transistors (OFETs). To achieve this objective, it is essential to design the key electron‐deficient units with simple structures and facile preparation processes, which can facilitate the production of low‐cost n‐type polymers. Herein, by sequentially introducing fluorine and cyano functionalities onto trans‐1,3‐butadiene, we developed a series of structurally simple but highly electron‐deficient building blocks, namely 1,4‐dicyano‐butadiene (CNDE), 3‐fluoro‐1,4‐dicyano‐butadiene (CNFDE), and 2,3‐difluoro‐1,4‐dicyano‐butadiene (CNDFDE), featuring a highly coplanar backbone and deep‐positioned lowest unoccupied molecular orbital (LUMO) energy levels (−3.03–4.33 eV), which render them highly attractive for developing n‐type semiconducting polymers. Notably, all these electron‐deficient units can be easily accessed by a two‐step high‐yield synthetic procedure from low‐cost raw materials, thus rendering them highly promising candidates for commercial applications. Upon polymerization with diketopyrrolopyrrole (DPP), three copolymers were developed that demonstrated unipolar n‐type transport characteristics in OFETs with the highest electron mobility of >1 cm2 V−1 s−1. Hence, CNDE, CNFDE, and CNDFDE represent a class of novel, simple, and efficient electron‐deficient units for constructing low‐cost n‐type polymers, thereby providing valuable insight for OFET applications.

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Section: Resultsmentioning

confidence: 99%

Semiconducting Polymers Based on Simple Electron‐Deficient Cyanated trans‐1,3‐Butadienes for Organic Field‐Effect Transistors

Chen

Wang

et al. 2023

Angew Chem Int Ed

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“…For the synthesis of 4,7-dibromo-2,1,3-benzothiadiazole (Zahara et al, 2020), the bromine (100.0 g, 0.63 mol) in HBr (150.0 mL, 48%) was dropwise added into a solution of benzothiadiazole (30.0 g, 0.22 mol) in HBr (300.0 mL, 48%) at room temperature. After the addition of bromine, the resulting milky reaction mixture was heated at 25 °C at reflux for 7 h. After the cooling of the mixture at room temperature, a saturated solution of Na 2 SO 3 (300.0 mL) was added dropwise for the removal of excess bromine.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

Metal-Free Pyrene-Based Conjugated Microporous Polymer Catalyst Bearing N- and S-Sites for Photoelectrochemical Oxygen Evolution Reaction

et al. 2021

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The development of an efficient, sustainable, and inexpensive metal-free catalyst for oxygen evolution reaction (OER) via photoelectrochemical water splitting is very demanding for energy conversion processes such as green fuel generators, fuel cells, and metal-air batteries. Herein, we have developed a metal-free pyrene-based nitrogen and sulfur containing conjugated microporous polymer having a high Brunauer-Emmett-Teller surface area (761 m2 g−1) and a low bandgap of 2.09 eV for oxygen evolution reaction (OER) in alkaline solution. The π-conjugated as-synthesized porous organic material (PBTDZ) has been characterized by Fourier transform infrared spectroscopy (FT-IR), solid-state 13C (cross-polarization magic angle spinning-nuclear magnetic resonance) CP-MAS NMR, N2 adsorption/desorption analysis, field-emission scanning electron microscope (FESEM), high-resolution transmission electron microscopy (HRTEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) experiments. The material acts as an efficient catalyst for photoelectrochemical OER with a current density of 80 mA/cm2 at 0.8 V vs. Ag/AgCl and delivered 104 µmol of oxygen in a 2 h run. The presence of low bandgap energy, π-conjugated conducting polymeric skeleton bearing donor heteroatoms (N and S), and higher specific surface area associated with inherent microporosity are responsible for this admirable photoelectrocatalytic activity of PBTDZ catalyst.

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“…Owing to their remarkable significance, developing convenient synthetic protocols for functionalized tetrahydrocarbazoles has attracted continual attention in synthetic and pharmaceutical chemistry [8][9][10][11][12][13][14][15]. Among many well-designed strategies for the synthesis of tetrahydrocarbazoles, the direct assembly of the tetrahydrocyclohexenyl ring with readily available functionalized indoles as pre-cursors has proven to be one of the most efficient synthetic protocols [16][17][18][19][20][21]. Therefore, many [4 + 2] reactions of 3-vinylindolines or 2-vinylindolines with diverse dienophiles have been successfully developed for the synthesis of many tetrahydrocarbazole and carbazole derivatives .…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

Zhan¹,

Fang²,

Sun³

et al. 2022

Beilstein J. Org. Chem.

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In the presence of copper sulfate, three- or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is an important development of the Levy reaction by using 2-methylindole to replace ethyl indole-2-acetate and successfully provides facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity.

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Programmed Sequential Additions to Halogenated Mucononitriles

Cited by 11 publications

References 42 publications

Semiconducting Polymers Based on Simple Electron‐Deficient Cyanated trans‐1,3‐Butadienes for Organic Field‐Effect Transistors

Semiconducting Polymers Based on Simple Electron‐Deficient Cyanated trans‐1,3‐Butadienes for Organic Field‐Effect Transistors

Metal-Free Pyrene-Based Conjugated Microporous Polymer Catalyst Bearing N- and S-Sites for Photoelectrochemical Oxygen Evolution Reaction

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

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