Heterocyclic Building Blocks-Benzothiophene

Zhang, Shaoqing published the artcileOver 14% Efficiency in Polymer Solar Cells Enabled by a Chlorinated Polymer Donor, SDS of cas: 1514905-24-8, the publication is Advanced Materials (Weinheim, Germany) (2018), 30(20), n/a, database is CAplus and MEDLINE.

Fluorine-contained polymers, which were widely used in highly efficient polymer solar cells (PSCs), are rather costly due to their complicated synthesis and low yields in the preparation of components. Here, the feasibility of replacing the critical fluorine substituents in high-performance photovoltaic polymer donors with chlorine is demonstrated, and two polymeric donors, PBDB-T-2F and PBDB-T-2Cl, are synthesized and compared in parallel. The synthesis of PBDB-T-2Cl is much simpler than that of PBDB-T-2F. The two polymers have similar optoelectronic and morphol. properties, except the chlorinated polymer possess lower mol. energy levels than the fluorinated one. As a result, the PBDB-T-2Cl-based PSCs exhibit higher open circuit voltage (V_oc) than the PBDB-T-2F-based devices, leading to an outstanding power conversion efficiency of over 14%. This work establishes a more economical design paradigm of replacing fluorine with chlorine for preparing highly efficient polymer donors.

Advanced Materials (Weinheim, Germany) published new progress about 1514905-24-8. 1514905-24-8 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BDT Donors, name is 4,8-Bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene, and the molecular formula is C10H14N2O, SDS of cas: 1514905-24-8.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Pan, Bo-Sheng published the artcileAn orally available non-nucleotide STING agonist with antitumor activity, Synthetic Route of 129425-81-6, the publication is Science (Washington, DC, United States) (2020), 369(6506), eaba6098, database is CAplus and MEDLINE.

Pharmacol. activation of the STING (stimulator of interferon genes)-controlled innate immune pathway is a promising therapeutic strategy for cancer. Here we report the identification of MSA-2, an orally available non-nucleotide human STING agonist. In syngeneic mouse tumor models, s.c. and oral MSA-2 regimens were well tolerated and stimulated interferon-β secretion in tumors, induced tumor regression with durable antitumor immunity, and synergized with anti-PD-1 therapy. Exptl. and theor. analyses showed that MSA-2 exists as interconverting monomers and dimers in solution, but only dimers bind and activate STING. This model was validated by using synthetic covalent MSA-2 dimers, which were potent agonists. Cellular potency of MSA-2 increased upon extracellular acidification, which mimics the tumor microenvironment. These properties appear to underpin the favorable activity and tolerability profiles of effective systemic administration of MSA-2.

Science (Washington, DC, United States) published new progress about 129425-81-6. 129425-81-6 belongs to benzothiophene, auxiliary class Inhibitor, name is 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid, and the molecular formula is C14H14O5S, Synthetic Route of 129425-81-6.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Mu, Delong published the artcileEnantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C-H silylation, Product Details of C12H14S, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(53), 7388-7391, database is CAplus and MEDLINE.

Herein, a rhodium-catalyzed desymmetrization of dihydrosilanes with heterocyclic compounds via intermol. dehydrogenative C-H silylation is developed. The strategy tolerates a variety of thianaphthene and thiophene derivatives, giving rise to a wide range of silicon-stereogenic acyclic monohydrosilanes. Several rare skeletons featuring bis-silicon-stereogenic centers were also designed to enhance the library’s diversity further. Preliminary mechanistic studies reveal that the surrounding spatial environment of the Si-center plays a crucial role in enabling intermol. C-H silylation preferentially.

Chemical Communications (Cambridge, United Kingdom) published new progress about 17515-00-3. 17515-00-3 belongs to benzothiophene, auxiliary class 5.6_Aromatics,Benzothiophens, name is 5-(tert-Butyl)benzo[b]thiophene, and the molecular formula is C12H14S, Product Details of C12H14S.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Ozaki, Kyohei published the artcileAnnulative π-extension (APEX) of heteroarenes with dibenzosiloles and dibenzogermoles by palladium/o-chloranil catalysis, Recommanded Product: 5-(tert-Butyl)benzo[b]thiophene, the publication is Organic Letters (2017), 19(7), 1930-1933, database is CAplus and MEDLINE.

Annulative π-extension (APEX) reactions of heteroarenes are described herein. A catalytic system comprising a cationic palladium species and o-chloranil using dimethyldibenzosiloles as π-extending agents enabled the extension of the π-system of benzo[b]thiophenes. π-Extended dibenzofurans and carbazoles could also be obtained from benzofuran and N-tosylindole, resp., with dimethyldibenzogermole as a germanium-based π-extending agent. Mechanistic investigations indicated two possible reaction pathways involving carbopalladation-based double C-H arylation of benzothiophene or formal cycloaddition/oxidation cascades.

Organic Letters published new progress about 17515-00-3. 17515-00-3 belongs to benzothiophene, auxiliary class 5.6_Aromatics,Benzothiophens, name is 5-(tert-Butyl)benzo[b]thiophene, and the molecular formula is C12H14S, Recommanded Product: 5-(tert-Butyl)benzo[b]thiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Wang, Xin published the artcilePalladium-Catalyzed Desymmetric Intermolecular C-N Coupling Enabled by a Chiral Monophosphine Ligand Derived from Anthracene Photodimer, Computed Properties of 177735-30-7, the publication is Organic Letters (2021), 23(14), 5485-5490, database is CAplus and MEDLINE.

An anthracene-photodimer-derived chiral monophosphine ligand I, which features dual chirality and a rigid scaffold was presented. This ligand exhibited remarkable efficiency in Pd-catalyzed desym. intermol. C-N coupling under mild conditions with excellent chemo- and enantioselectivity.

Organic Letters published new progress about 177735-30-7. 177735-30-7 belongs to benzothiophene, auxiliary class Boronic acid and ester,Benzothiophene,Boronic Acids,Boronic acid and ester, name is (1-Benzothiophen-4-yl)boronic acid, and the molecular formula is C8H8O3, Computed Properties of 177735-30-7.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Chen, Zhongxin published the artcileEvolution of the electronic structure in open-shell donor-acceptor organic semiconductors, Recommanded Product: 4,8-Bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, the publication is Nature Communications (2021), 12(1), 5889, database is CAplus and MEDLINE.

The donor-acceptor organic semiconductors comprised of diketopyrrolopyrrole and naphthobisthiadiazole acceptors and various electron-rich donors commonly utilized in constructing high-performance organic semiconductors were reported. NMR, ESR, magnetic susceptibility measurements, single-crystal X-ray studies and computational investigations connect the bandgap, π-extension, structural and electronic features with the emergence of various degrees of diradical character. This work systematically demonstrates the widespread diradical character in the classical donor-acceptor organic semiconductors and provides distinctive insights into their ground state structure-property relationship.

Nature Communications published new progress about 1401018-41-4. 1401018-41-4 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BT Acceptors, name is 4,8-Bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, and the molecular formula is C30H36Br2N4S4, Recommanded Product: 4,8-Bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Zhao, Wenchao published the artcileMolecular Optimization Enables over 13% Efficiency in Organic Solar Cells, COA of Formula: C34H40F2S4, the publication is Journal of the American Chemical Society (2017), 139(21), 7148-7151, database is CAplus and MEDLINE.

A new polymer donor (PBDB-T-SF) and a new small mol. acceptor (IT-4F) for fullerene-free organic solar cells (OSCs) were designed and synthesized. The influences of fluorination on the absorption spectra, mol. energy levels, and charge mobilities of the donor and acceptor were systematically studied. The PBDB-T-SF:IT-4F-based OSC device showed a record high efficiency of 13.1%, and an efficiency of over 12% can be obtained with a thickness of 100-200 nm, suggesting the promise of fullerene-free OSCs in practical applications.

Journal of the American Chemical Society published new progress about 1514905-24-8. 1514905-24-8 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BDT Donors, name is 4,8-Bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene, and the molecular formula is C15H23BO2, COA of Formula: C34H40F2S4.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Wu, Yingtao published the artcileSynthesis of Axially Chiral Aldehydes by N-Heterocyclic-Carbene-Catalyzed Desymmetrization Followed by Kinetic Resolution, Name: Benzo[b]thiophen-7-ylboronic acid, the publication is Angewandte Chemie, International Edition (2022), 61(14), e202117340, database is CAplus and MEDLINE.

Herein an NHC-catalyzed atroposelective esterification of biaryl dialdehydes as a general and practical strategy for the construction of axially chiral aldehydes I [Ar = Ph, 1-naphthyl, 9-phenanthryl, etc.; R¹ = Et, CH₂CF₃, cyclopropyl, etc.] was described. Mechanistic studies indicated that coupling proceeds through a novel combination of NHC-catalyzed desymmetrization of the dialdehydes and kinetic resolution This protocol featured excellent enantioselectivity, mild conditions, good functional-group tolerance and applicability to late-stage functionalization and provided a modular platform for the synthesis of axially chiral aldehydes and their derivatives

Angewandte Chemie, International Edition published new progress about 628692-17-1. 628692-17-1 belongs to benzothiophene, auxiliary class Boronic acid and ester,Benzothiophene,Benzothiophene,Boronic Acids,Boronic Acids,Boronic acid and ester, name is Benzo[b]thiophen-7-ylboronic acid, and the molecular formula is C12H14O2, Name: Benzo[b]thiophen-7-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

He, Shasha published the artcileCharge-Reversal Polymer Nano-modulators for Photodynamic Immunotherapy of Cancer, Related Products of benzothiophene, the publication is Angewandte Chemie, International Edition (2021), 60(35), 19355-19363, database is CAplus and MEDLINE.

Nanomedicine can regulate the balance between cytotoxic T lymphocytes (CTLs) and suppressive regulatory T lymphocytes (Tregs), which however has been rarely exploited for cancer immunotherapy. We report a charge-reversal polymer nano-modulator (SPDMCN) activated by tumor microenvironment (TME) for photodynamic immunotherapy of cancer. SPDMCN is constructed by conjugating an immunomodulator (demethylcantharidin, DMC) to the side chains of a photodynamic polymer via an acid-liable linker. The neg. charge of SPDMCN ensures its high stability in blood circulation and ideal tumor accumulation; exposure to acidic TME reverses its surface charge to pos., enhancing tumor penetration and locally releasing DMC. Upon near-IR photoirradiation, SPDMCN generates singlet oxygen to ablate tumors and promote maturation of dendritic cells. Released DMC inhibits protein phosphatase 2 (PP2A) activity and decreases Tregs differentiation. Such combinational action induces a sharp increase in CTL/Treg ratio in TME and effectively inhibits both primary and distant tumors in living mice.

Angewandte Chemie, International Edition published new progress about 1426829-76-6. 1426829-76-6 belongs to benzothiophene, auxiliary class Other Aromatic Heterocyclic,Bromide, name is 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, and the molecular formula is C21H26Br4S2, Related Products of benzothiophene.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem

Huber, Johannes published the artcileNanoparticles of Low Optical Band Gap Conjugated Polymers, Computed Properties of 1401018-41-4, the publication is Macromolecules (Washington, DC, United States) (2012), 45(19), 7799-7805, database is CAplus.

Sonogashira coupling of 9,9-bis(2-ethylhexyl)-2,7-diethynyl-9H-fluorene (1) with 2,7-dibromo-9,9-bis(2-ethylhexyl)-9H-fluorene (2) and dibromo-substituted electron accepting arylenes 5,7-bis(5-bromothiophen-2-yl)-2,3-dihexylthieno[3,4-b]pyrazine (3), 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)bis(benzothiadiazole) (4) or 4,9-bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)-6,7-dihexylthiadiazolo[3,4-g]quinoxaline (5), resp., in a miniemulsion polymerization process afforded colloidally stable dispersions of poly(arylene ethynylene) nanoparticles with an average size in the range of 50 to 120 nm. For these poly[1-alt-(2-co-X)] (X = 3, 4, or 5), poly(1-alt-3), poly(1-alt-4), and poly(1-alt-5) aqueous nanoparticle dispersions absorption occurs increasingly in the red and NIR regime with increasing incorporation of acceptor monomer, with a strong absorption up to λ_abs = 1 μm for poly(1-alt-4) dispersions. For poly[1-alt-(2-co-3)] nanoparticles fluorescence is also observed at λ_em = ca. 700 nm, which occurs at this long wavelength exclusively even at an incorporation of only 1 mol % of 3 due to energy transfer to the low-energy chromophores. An alternative postpolymn. approach by change of solvent quality yielded dilute aqueous dispersions of self-stabilized nanoparticles from an amphiphilic block copolymer, poly(ethylene glycol)-block-poly(1-alt-6)-block-poly(ethylene glycol) generated from alkyne-terminated poly(1-alt-6) via azide-alkyne coupling (6 = 4,7-bis(5-bromo-4-(2-ethylhexyl)thiophene-2-yl)benzothiadiazole), which fluoresce at λ_em max = 672 nm.

Macromolecules (Washington, DC, United States) published new progress about 1401018-41-4. 1401018-41-4 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BT Acceptors, name is 4,8-Bis(5-bromo-4-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, and the molecular formula is C30H36Br2N4S4, Computed Properties of 1401018-41-4.

Referemce:
https://en.wikipedia.org/wiki/Benzothiophene,
Benzothiophene | C8H6S – PubChem