Category: benzothiophene

Zhang, Maojie published the artcileA Large-Bandgap Conjugated Polymer for Versatile Photovoltaic Applications with High Performance, Quality Control of 1514905-24-8, the publication is Advanced Materials (Weinheim, Germany) (2015), 27(31), 4655-4660, database is CAplus and MEDLINE.

Herein, we synthesized a new copolymer PM6 based on 4,8-bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene(BDT-F) and 1,3-bis(thiophen-2-yl)-5,7-bis(2-ethylhexyl)benzo-[1,2-c:4,5-c’]dithiophene-4,8-dione (BDD). The optical, electrochem., and photovoltaic properties, the mol. packing pattern, and the morphol. of the blend lms were investigated. Compared with the nonfluorinated derivative PBDTBDD, PM6 exhibited a similar optical bandgap of 1.80 eV and a deeper HOMO level of -5.45 eV (-5.25 eV for PBDTBDD), which is beneficial for a high V_oc. BHJ PSCs based on PM6/PC71 BM with both conventional and inverted device structures were fabricated and showed promising photovoltaic performance: a high V_oc of 0.98 V and a PCE of 8% for the conventional devices and up to 9.2% for the inverted devices. Furthermore, the PM6/PC71BM based semitransparent device exhibited a PCE of 5.7%, which is among the highest values obtained for a semitransparent single-junction device. In addition, we found that the neat film of PM6 exhibited strong crystallinity and a dominant face on packing with respect to the electrodes, which is advantageous for charge transport. These results indicate that PM6 is a promising material for photovoltaic application.

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 C12H9N3O4, Quality Control of 1514905-24-8.

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

Zhang, Maojie published the artcileSynergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers, Safety of 4,8-Bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene, the publication is Advanced Materials (Weinheim, Germany) (2014), 26(7), 1118-1123, database is CAplus and MEDLINE.

Four newly designed donor-acceptor polymers were prepared and characterized. The results clearly, show that fluorination on the donor and the acceptor moieties has little influence on the optical properties, but a synergistic effect on lowering their mol. energy levels. Accordingly, the photovoltaic measurements show that the PSC (polymer solar cell) device based on the tri- P2fluorinated polymer, PBT-3F, shows an enhanced PCE of 8.6%, which is among the highest for PSCs with a single heterojuncνtion structure. Therefore, introducing fluorine atoms onto the appropriate positions of the donor units in D-A polymers will be a promising method to effectively tune their mol. energy levels of for applications in PSCs.

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 C12H14BNO2, Safety of 4,8-Bis(5-(2-ethylhexyl)-4-fluorothiophen-2-yl)benzo[1,2-b:4,5-b’]dithiophene.

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

Lyu, Yan published the artcileA Photolabile Semiconducting Polymer Nanotransducer for Near-Infrared Regulation of CRISPR/Cas9 Gene Editing, COA of Formula: C21H26Br4S2, the publication is Angewandte Chemie, International Edition (2019), 58(50), 18197-18201, database is CAplus and MEDLINE.

Noninvasive regulation of CRISPR/Cas9 gene editing is conducive to understanding of gene function and development of gene therapy; however, it remains challenging. Herein, a photolabile semiconducting polymer nanotransducer (pSPN) is synthesized to act as the gene vector to deliver CRISPR/Cas9 plasmids into cells and also as the photoregulator to remotely activate gene editing. pSPN comprises a ¹O₂-generating backbone grafted with polyethylenimine brushes through ¹O₂-cleavable linkers. NIR photoirradiation spontaneously triggers the cleavage of gene vectors from pSPN, resulting in the release of CRISPR/Cas9 plasmids and subsequently initiating gene editing. This system affords 15- and 1.8-fold enhancement in repaired gene expression relative to the nonirradiated controls in living cells and mice, resp. As this approach does not require any specific modifications on biomol. components, pSPN represents the first generic nanotransducer for in vivo regulation of CRISPR/Cas9 gene editing.

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, COA of Formula: C21H26Br4S2.

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

Zhang, Yan published the artcileActivatable Polymeric Nanoprobe for Near-Infrared Fluorescence and Photoacoustic Imaging of T Lymphocytes, Synthetic Route of 1426829-76-6, the publication is Angewandte Chemie, International Edition (2021), 60(11), 5921-5927, database is CAplus and MEDLINE.

Development of real-time non-invasive imaging probes to assess infiltration and activation of cytotoxic T cells (CTLs) is critical to predict the efficacy of cancer immunotherapy, which however remains challenging. Reported here is an activatable semiconducting polymer nanoprobe (SPNP) for near-IR fluorescence (NIRF) and photoacoustic (PA) imaging of a biomarker (granzyme B) associated with activation of CTLs. SPNP comprises a semiconducting polymer (SP) conjugated with a granzyme B cleavable and dye-labeled peptide as the side chain, both of which emit NIRF and PA signals. After systemic administration, SPNP passively targets the tumor and in situ reacts with granzyme B to release the dye-labeled peptide, leading to decreased NIRF and PA signals from the dye but unchanged signals from the polymer. Such ratiometric NIRF and PA signals of SPNP correlate well with the expression level of granzyme B and intratumoral population of CTLs. Thus, this study not only presents the first PA probes for in vivo imaging of immune activation but also provides a mol. design strategy that can be generalized for mol. imaging of other immune-related biomarkers.

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 C7H11N, Synthetic Route of 1426829-76-6.

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

Syeda, Madiha Zahra published the artcileA prodrug nanoplatform via esterification of STING agonist and IDO inhibitor for synergistic cancer immunotherapy, Name: 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid, the publication is Nano Research, database is CAplus.

Cancer immunotherapy has made significant progress in the last few decades, revolutionizing oncol. However, low patient response rates and potential immune-related adverse events continue to be major clin. challenges. Cancer nanomedicine, by virtue of its regulated delivery and modular flexibility, has shown the potential to strengthen antitumor immune responses and sensitize tumors to immunotherapy. In this study, we developed tumor microenvironment (TME) responsive nanomedicine to achieve specific and localized amplification of the immune response in tumor tissue in a safe and effective manner, while simultaneously reducing immune-related side effects. We synthesized the TME responsive prodrug by coupling MSA-2, a stimulator of interferon genes (STING) agonist, and NLG-919, an indoleamine 2,3 dioxygenase (IDO) inhibitor. The prodrug was assembled into nanoparticles to enhance the solubility and bioavailability. By synthesizing a TME responsive prodrug, we aim to explore the therapeutic efficacy of combined regimen (STING agonist and IDO inhibitor) for cancer, and reduce the unwanted side effects of STING agonism on normal tissues. Free prodrug and nanoparticles were characterized by mass spectrometry, dynamic light scattering (DLS), and transmission electron microscopy (TEM). Following that, we investigated the tumor accumulation, anti-tumor activity, and toxicity in vitro and in vivo. Prodrug nanoparticles demonstrated the ability to inhibit the tumor growth and activate antitumor immune response by modulating immune cells populations in tumor microenvironment. The TME responsive nanomedicine provided an effective tool for precise targeting, promoting antitumor immunity, and efficient tumor growth inhibition with safety. Outcomes of this study may have implications for future clin. trials.

Nano Research 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 C5H7NO, Name: 4-(5,6-Dimethoxybenzo[b]thiophen-2-yl)-4-oxobutanoic acid.

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

Li, Jingchao published the artcilePhotoactivatable Organic Semiconducting Pro-nanoenzymes, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Journal of the American Chemical Society (2019), 141(9), 4073-4079, database is CAplus and MEDLINE.

Therapeutic enzymes hold great promise for cancer therapy; however, in vivo remote control of enzymic activity to improve their therapeutic specificity remains challenging. This study reports the development of an organic semiconducting pro-nanoenzyme (OSPE) with a photoactivatable feature for metastasis-inhibited cancer therapy. Upon near-IR (NIR) light irradiation, this pro-nanoenzyme not only generates cytotoxic singlet oxygen (¹O₂) for photodynamic therapy (PDT), but also triggers a spontaneous cascade reaction to induce the degradation of RNA specifically in tumor microenvironment. More importantly, OSPE-mediated RNA degradation is found to downregulate the expression of metastasis-related proteins, contributing to the inhibition of metastasis after treatment. Such a photoactivated and cancer-specific synergistic therapeutic action of OSPE enables complete inhibition of tumor growth and lung metastasis in mouse xenograft model, which is not possible for the counterpart PDT nanoagent. Thus, our study proposes a phototherapeutic-proenzyme approach toward complete-remission cancer therapy.

Journal of the American Chemical Society 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, Safety of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

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

Matsuoka, Wataru published the artcileRapid Access to Nanographenes and Fused Heteroaromatics by Palladium-Catalyzed Annulative π-Extension Reaction of Unfunctionalized Aromatics with Diiodobiaryls, Name: 5-(tert-Butyl)benzo[b]thiophene, the publication is Angewandte Chemie, International Edition (2017), 56(40), 12224-12228, database is CAplus and MEDLINE.

Efficient and rapid access to nanographenes and π-extended fused heteroaromatics is important in materials science. Herein, we report a palladium-catalyzed efficient one-step annulative π-extension (APEX) reaction of polycyclic aromatic hydrocarbons (PAHs) and heteroaromatics, producing various π-extended aromatics In the presence of a cationic Pd complex, triflic acid, silver pivalate, and diiodobiaryls, diverse unfunctionalized PAHs and heteroaromatics were directly transformed into larger PAHs, nanographenes, and π-extended fused heteroaromatics in a single step. In the reactions that afford [5]helicene substructures, simultaneous dehydrogenative ring closures occur at the fjord regions to form unprecedented larger nanographenes. This successive APEX reaction is notable as it stiches five aryl-aryl bonds by C-H functionalization in a single operation. Moreover, the unique mol. structures, crystal-packing structures, photophys. properties, and frontier MOs of the thus-formed nanographenes were elucidated.

Angewandte Chemie, International Edition 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, Name: 5-(tert-Butyl)benzo[b]thiophene.

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

Xu, Cheng published the artcileSecond Near-Infrared Light-Activatable Polymeric Nanoantagonist for Photothermal Immunometabolic Cancer Therapy, HPLC of Formula: 1426829-76-6, the publication is Advanced Materials (Weinheim, Germany) (2021), 33(36), 2101410, database is CAplus and MEDLINE.

Immunometabolic modulation offers new opportunities to treat cancers as it is highly associated with cancer progression and immunosuppressive microenvironment. However, traditional regimens using nonselective small-mol. immunomodulators lead to the off-target adverse effects and insufficient therapeutic outcomes. Herein a second near-IR (NIR-II) photothermally activatable semiconducting polymeric nanoantagonist (ASPA) for synergistic photothermal immunometabolic therapy of cancer is reported. ASPA backbone is obtained by conjugating vipadenant, an antagonist to adenosine A2A receptor, onto NIR-II light-absorbing semiconducting polymer via an azo-based thermolabile linker. Under deep-penetrating NIR-II photoirradiation, ASPA induces tumor thermal ablation and subsequently immunogenic cell death, triggers the cleavage of thermolabile linker, and releases the antagonist to block the immunosuppressive adenosinergic pathway. Such a remotely controlled immunometabolic regulation potentiates cytotoxic T cell functions while suppresses regulatory T cell activities, leading to efficient primary tumor inhibition, pulmonary metastasis prevention, and long-term immunol. memory. Thereby, this work provides a generic polymeric approach for precise spatiotemporal regulation of cancer immunometabolism.

Advanced Materials (Weinheim, Germany) 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 C5H10Cl3O3P, HPLC of Formula: 1426829-76-6.

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

Zhang, Zhongqiang published the artcilePhosphate ester side-chain modified conjugated polymer for hybrid solar cells, Application of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene, the publication is Journal of Applied Polymer Science (2017), 134(26), n/a, database is CAplus.

Although nanocrystals have several advantages of tunable bandgap and high carrier mobility, it is still challenging to achieve high-performance polymer: nanocrystals hybrid solar cells (HSC) due to the complicated surface problem. Many efforts have been devoted to replace the long alkyl chain on the surface of nanocrystals to improve the charge transfer and transport. We modified the alkyl chain in poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b’]-dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT) by phosphate ester. Due to its strong affinity to CdSe nanocrystals, the resulting polymers can spontaneously exchange the long chain ligands in 1-step process. With the improved morphol. of polymer: CdSe blended film, a power conversion efficiency (PCE) of 3.12% was achieved for hybrid solar cells. © 2017 Wiley Periodicals, Inc., J. Appl. Polym. Sci. 2017, 134, 45003.

Journal of Applied Polymer Science 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 0, Application of 2,6-Dibromo-4,4-bis(6-bromohexyl)-4H-cyclopenta[1,2-b:5,4-b’]dithiophene.

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

Huber, Johannes published the artcileNanoparticles of Low Optical Band Gap Conjugated Polymers, Quality Control of 1401018-39-0, 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 1401018-39-0. 1401018-39-0 belongs to benzothiophene, auxiliary class Organic Photo-Voltaic Materials, OPV,BT Acceptors, name is 2Lambda4delta2-Benzo[1,2-c:4,5-c’]bis[1,2,5]thiadiazole, 4,8-bis[4-(2-ethylhexyl)-2-thienyl]-, and the molecular formula is C30H38N4S4, Quality Control of 1401018-39-0.

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