Regioselective copper-catalyzed direct arylation of benzodithiophene-S,S-tetraoxide

Khambhati, Devang P.; Sachinthani, K. A. Niradha; Rheingold, Arnold L.; Nelson, Toby L.

doi:10.1039/c7cc01781b

Cited by 20 publications

(17 citation statements)

References 26 publications

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“… 29 For copper catalysis, direct arylation of benzodithiophene- S , S -tetraoxide with aryl iodides was found to be most efficient with Ag 2 CO 3 . 30 In a subsequent computation study, it was determined that the Ag additive reduces the rate-limiting Ph–I insertion through a Ag–I interaction and oxidative addition of Ph–I on Ag. 31 For Cu-catalyzed amide arylations using excess bidentate ligands, Ar–I insertion is rate-limiting.…”

Section: Results and Discussionmentioning

confidence: 99%

Silver Benzoate Facilitates the Copper-Catalyzed C–N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles

et al. 2021

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In the literature, C–N coupling methods for the reaction of iodo-oxazole with 2-pyridinone were found to be low yielding. C–N coupling using silver benzoate additives with CuI catalysts and 4,7-dimethoxy-1,10-phenanthroline ligands has been developed to afford synthetically useful yields of the desired heterobicycle product. The reaction conditions are applied to the coupling of a range of iodo-heterocycles with 2-pyridinone. The coupling of a variety of NH-containing heterocycles with 4-iodo-oxazole is also demonstrated. The use of 2-, 4-, or 5-iodo-oxazole allows for the coupling of pyridinone to each oxazole position.

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Section: Results and Discussionmentioning

confidence: 99%

Silver Benzoate Facilitates the Copper-Catalyzed C–N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles

et al. 2021

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“…In attempts to further increase the M n of P1, we noted that Cu I salts have been extensively used as a catalyst or activator for the direct arylation of N‐heteroarenes– and other electron deficient arenes . For example, Miura et al.…”

Section: Resultsmentioning

confidence: 99%

Significant Difference in Semiconducting Properties of Isomeric All‐Acceptor Polymers Synthesized via Direct Arylation Polycondensation

et al. 2019

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The direct arylation polycondensation (DArP) appeared as an efficient method for producing semiconducting polymers but often requires acceptor monomers with orienting or activating groups for the reactive carbon-hydrogen (C-H) bonds,w hichl imits the choice of acceptor units.I nt his study, we describe aD ArP for producing high-molecular-weight allacceptor polymers composed of the acceptor monomers without any orienting or activating groups via am odified method using Pd/Cu co-catalysts.W et hus obtained two isomeric all-acceptor polymers,P 1a nd P2, which have the same backbone and side-chains but different positions of the nitrogen atoms in the thiazole units.T his subtle change significantly influences their optoelectronic,m olecular packing, and charge-transport properties.P 2w ith ag reater backbone torsion has favorable edge-on orientations and ah igh electron mobility m e of 2.55 cm 2 V À1 s À1 .M oreover,P 2-based transistors show an excellent shelf-storage stability in air even after the storage for 1month.

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“…All reagents were obtained from commercial vendors and used as received unless otherwise stated. The synthetic pathways for BDTT, T 3 , and TEDOT 2 monomers were adopted from previously reported literature [27,30,31,43] and outlined in the Supporting Information (Figure S1-S3). The Photophysical properties of BDTT is reported in Supporting Information (Figure S4).…”

Section: Experimental Section Materialsmentioning

confidence: 99%

“…[29,30] Despite its limited synthetic accessibility, BDTT was previously implemented in direct arylation studies for regioselective functionalization and proven as an efficient acceptor in D-A type molecular strategy for n-type materials. [30,31] Interestingly, its electrochemical synthesis and conductivity have not been studied. We, in turn, electropolymerized it using 3,4-ethylenedioxythiophene flanked thiophene (TEDOT 2 ) and T 3 as our donor monomer.…”

Section: Introductionmentioning

confidence: 99%

“…BDTT has seen limited utility as a building block for conjugated materials due to difficulties in chemical functionalization and low yields [29,30] . Despite its limited synthetic accessibility, BDTT was previously implemented in direct arylation studies for regioselective functionalization and proven as an efficient acceptor in D‐A type molecular strategy for n‐type materials [30,31] . Interestingly, its electrochemical synthesis and conductivity have not been studied.…”

Section: Introductionmentioning

confidence: 99%

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Benzodithiophene‐S,S‐tetraoxide (BDTT) as an Acceptor Towards Donor‐Acceptor (D‐A)‐Type Semiconducting Electropolymers

et al. 2021

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This study introduces a benzodithiophene-S,S-tetraoxide (BDTT) monomer as an acceptor and 3,4-ethylenedioxythiophene flanked thiophene (TEDOT 2) and terthiophene (T 3) as donor molecules for polymer formation. The synthesis of the poly (TEDOT 2-BDTT) and poly(T 3-BDTT) copolymers was performed via a single-step monomer radical formation that is typically associated with electropolymerization methods. The electropolymerization is controlled by using a suitable monomer stoichiometric ratio that enables the deposition of copolymer thin films on the working electrode. Resultant copolymers were investigated by electrochemical analysis and their electronic properties are discussed in detail. A low average electron transport resistance of 16.5 Ω was found for poly(TEDOT 2-BDTT), indicating excellent conductive behavior. Solid-state absorbance and emission studies of the copolymers show visible to near-infrared spectral activity. Results support an effective strategy towards highly efficient electronically conducting polymers (ECPs) based on a unique BDTT monomer.

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Regioselective copper-catalyzed direct arylation of benzodithiophene-S,S-tetraoxide

Cited by 20 publications

References 26 publications

Silver Benzoate Facilitates the Copper-Catalyzed C–N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles

Silver Benzoate Facilitates the Copper-Catalyzed C–N Coupling of Iodoazoles with Aromatic Nitrogen Heterocycles

Significant Difference in Semiconducting Properties of Isomeric All‐Acceptor Polymers Synthesized via Direct Arylation Polycondensation

Benzodithiophene‐S,S‐tetraoxide (BDTT) as an Acceptor Towards Donor‐Acceptor (D‐A)‐Type Semiconducting Electropolymers

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