Category: 239075-02-6

Porzio, William published the artcileClose Packing in Crystals of Cyanophenylene/Thienylene Derivatives, COA of Formula: C20H28B2O4S2, the publication is Crystal Growth & Design (2006), 6(6), 1497-1503, database is CAplus.

A new mol., designed as a potential active material in field effect transistor (FET) devices and constituted by p-cyanophenylene and -thienylene residues, was synthesized and characterized by electrochem., photophys., and structural points of view. Its crystal structure, derived from powder XRD data, displays higher close packing as compared with mol. crystals constituted by similar residues. The crystallization aptness was demonstrated by growing solid films, from 15 nm to 2 μm thick, using high vacuum depositions, casting, and spin coating techniques. AFM study shows well formed needles, univocally oriented with respect to the substrate. The HOMO/LUMO levels, matching the electrode working function, the film orientation, and the close packing, suggest its promising use as an active layer in FET devices.

Crystal Growth & Design published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, COA of Formula: C20H28B2O4S2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bagutski, Viktor published the artcileMechanistic studies into amine-mediated electrophilic arene borylation and its application in MIDA boronate synthesis, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Journal of the American Chemical Society (2013), 135(1), 474-487, database is CAplus and MEDLINE.

Direct electrophilic borylation using Y₂BCl (Y₂ = Cl₂ or o-catecholato) with equimolar AlCl₃ and a tertiary amine has been applied to a wide range of arenes and heteroarenes, yielding aryl and heterocyclic boronates in a regioselective way. In situ functionalization of the ArBCl₂ products is possible with Me₃SiOCOCH₂NMeCH₂CO₂SiMe₃ (TMS₂MIDA), to afford bench-stable and easily isolable MIDA-boronates in moderate to good yields; pinacol and neopentylglycol esters were also prepared According to a combined exptl. and computational study, the borylation of activated arenes at 20° proceeds through an S_EAr mechanism with borenium cations, [Y₂B(amine)]⁺, the key electrophiles. For catecholato-borocations, two amine dependent reaction pathways were identified: with [CatB(NEt₃)]⁺, an addnl. base is necessary to accomplish rapid borylation by deprotonation of the borylated arenium cation (σ complex), which otherwise would rather decompose to the starting materials than liberate the free amine to effect deprotonation. Apart from amines, the addnl. base may also be the arene itself when it is sufficiently basic (e.g., N-Me-indole). When the amine component of the borocation is less nucleophilic (e.g., 2,6-lutidine), no addnl. base is required due to more facile amine dissociation from the boron center in the borylated arenium cation intermediate. Borenium cations do not borylate poorly activated arenes (e.g., toluene) even at high temperatures; instead, the key electrophile in this case involves the product from interaction of AlCl₃ with Y₂BCl. When an extremely bulky amine is used, borylation again does not proceed via a borenium cation; instead, a number of mechanisms are feasible including via a boron electrophile generated by coordination of AlCl₃ to Y₂BCl, or by initial (heteroarene)AlCl₃ adduct formation followed by deprotonation and transmetalation.

Journal of the American Chemical Society published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Lee, Jonghee published the artcileEnhanced efficiency of polyfluorene derivatives: organic-inorganic hybrid polymer light-emitting diodes, Safety of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (2006), 44(9), 2943-2954, database is CAplus.

Two novel organic-inorganic hybrid polyfluorene derivatives, poly{(9,9′-dioctyl-2,7-fluorene)-co-(9,9′-di-POSS-2,7-fluorene)-co-[2,5-bis(octyloxy)-1,4-phenylene]} (PFDOPPOSS) and poly{(9,9′-dioctyl-2,7-fluorene)-co-(9,9′-di-POSS-2,7-fluorene)-co-bithiophene} (PFT2POSS), were synthesized by the Pd-catalyzed Suzuki reaction of polyhedral oligomeric silsesquioxane (POSS) appended fluorene, dioctyl phenylene, and bithiophene moieties. The synthesized polymers were characterized with ¹H NMR spectroscopy and elemental anal. Photoluminescence (PL) studies showed that the incorporation of the POSS pendant into the polyfluorene derivatives significantly enhanced the fluorescence quantum yields of the polymer films, likely via a reduction in the degree of interchain interaction as well as keto formation. Addnl., the blue-light-emitting polyfluorene derivative PFDOPPOSS showed high thermal color stability in PL. Moreover, single-layer light-emitting diode devices of an indium tin oxide/poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate)/polymer/Ca/Al configuration fabricated with PFDOPPOSS and PFT2POSS showed much improved brightness, maximum luminescence intensity, and quantum efficiency in comparison with devices fabricated with the corresponding pristine polymers PFDOP and PFT2. In particular, the maximum external quantum efficiency of PFT2POSS was 0.13%, which was twice that of PFT2 (0.06%), and the maximum current efficiency of PFT2POSS was 0.38 cd/A, which again was twice that of PFT2 (0.19 cd/A).

Journal of Polymer Science, Part A: Polymer Chemistry published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Safety of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gallaher, Joseph K. published the artcileEvolution of Nonmirror Image Fluorescence Spectra in Conjugated Polymers and Oligomers, Quality Control of 239075-02-6, the publication is Journal of Physical Chemistry Letters (2016), 7(17), 3307-3312, database is CAplus and MEDLINE.

The nonmirror image relation between absorption and fluorescence spectra of conjugated polymers contrasts with most organic chromophores and is widely considered a signature of interchromopohore energy funneling. The authors apply broad-band ultrafast fluorescence spectroscopy to resolve the evolution of fluorescence spectra for dilute solutions of conjugated oligothiophenes, where no energy transfer is possible. Fluorescence spectra evolve from a mirror image of absorption, which lacks vibronic structure, toward a spectrally narrower and vibronically structured species on the hundreds of femtosecond to early picosecond time scale. The authors’ anal. of this fluorescence spectral evolution shows that a broad distribution of torsional conformers is driven to rapidly planarize in the excited state, including in solid films, which is supported by Raman spectroscopy and quantum chem. modeling. The authors’ data have important implications for understanding different energy-transfer regimes that are delineated by structural relaxation.

Journal of Physical Chemistry Letters published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Quality Control of 239075-02-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jiang, Kang published the artcileExploring functionalized polythiophene derivatives based on thiophene-linker-thiophene platform, analysis of prototype monomer crystal for C-Br/C-H bulk polycondensation and its application for acid detection, Name: 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Polymer (2019), 70-76, database is CAplus.

Ten thiophene derivatives monomers were designed based on thiophene-linker-thiophene platform and were subjected to C-Br/C-H bulk polycondensation. All of them were converted to corresponding polythiophene derivatives smoothly, indicating that up to three-building-blocks of thiophene monomers can be successfully constructed. Detailed characterizations of the obtained polymers were carried out by regular measurements, including Cyclic Voltammetry (CV), IR spectrum (IR), UV-Vis absorbance spectroscopy, TGA and so on. In addition, the obtained poly{phenyl-bis-(4-thiophen-2-yl-phenyl)-amine} was employed as acid sensor and the results showed that HNO₃ acid could be recognized and distinguished successfully. Furthermore, a prototype monomer crystal of 2-bromo-3-(9,9-dimethyl-9H-fluoren-2-yl)-thiophene is obtained and its effective reaction points distance (4.197 Å) is longer (37.6%) than the van der Waals radius (rw) of reaction points (sum of rw of bromine and hydrogen atoms 3.05 Å).

Polymer published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Name: 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Colella, L. published the artcileOutside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Physical Chemistry Chemical Physics (2015), 17(16), 10426-10437, database is CAplus and MEDLINE.

The biradicaloid vs. quinoidal character of the ground state of thiophene-based heterophenoquinones bearing donor or acceptor groups is investigated. Keeping the conjugation length fixed, namely, the 5,5′-bis(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-2,2′-dihydroxy bithiophene backbone, an opposite effect occurs depending on the donating or withdrawing nature of the substituents. The character of the ground state depends not only on the electronic nature of the substituents but also on their position on the mol. skeleton: donor groups on the 3,3′-positions of the bithiophene central core stabilize a quinoidal ground state, whereas a biradicaloid electronic structure results from the introduction of the same donor groups onto the lateral phenones. Withdrawing groups behave similar to donors, but in the opposite direction.

Physical Chemistry Chemical Physics published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Application of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Melucci, Manuela published the artcileSolvent-Free, Microwave-Assisted Synthesis of Thiophene Oligomers via Suzuki Coupling, Quality Control of 239075-02-6, the publication is Journal of Organic Chemistry (2002), 67(25), 8877-8884, database is CAplus and MEDLINE.

The purpose of this study was to obtain a rapid, efficient, and environmentally friendly methodol. for the synthesis of highly pure thiophene oligomers. The solvent-free, microwave-assisted coupling of thienyl boronic acids and esters with thienyl bromides, using aluminum oxide as the solid support, allowed us to rapidly check the reaction trends on changing times, temperature, catalyst, and base and easily optimize the exptl. conditions to obtain the targeted product in fair amounts This procedure offers a novel, general, and very rapid route to the preparation of soluble thiophene oligomers. Thus, for example, quaterthiophene was obtained in 6 min by reaction of 2-bromo-2,2′-bithiophene with bis(pinacolato)diboron (isolated yield 65%), whereas quinquethiophene was obtained in 11 min by reaction of dibromoterthiophene with thienylboronic acid (isolated yield 74%). The synthesis of new chiral 2,2′-bithiophenes is reported. The detailed anal. of the byproducts of some reactions allowed us to elucidate a few aspects of reaction mechanisms. While the use of microwaves proved to be very convenient for the coupling between conventional thienyl moieties, the same was not true for the coupling of thienyl rings to thienyl-S,S-dioxide moieties. Indeed, in this case, the targeted product was obtained in low yields because of the competitive, accelerated, Diels-Alder reaction that affords a variety of condensation products.

Journal of Organic Chemistry published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Quality Control of 239075-02-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Stas, Sara published the artcileStraightforward access to diketopyrrolopyrrole (DPP) dimers, Formula: C20H28B2O4S2, the publication is Dyes and Pigments (2013), 97(1), 198-208, database is CAplus.

Synthesis, isolation and characterization of diketopyrrolopyrrole (DPP) dimers are described. These derivatives were prepared starting from sym. or asym. diketopyrrolopyrrole monomers through Pd-catalyzed homocoupling, Yamamoto coupling or Suzuki coupling. The spectroscopic properties of these newly synthesized DPP dimers were investigated and were supported by quantum-chem. calculations

Dyes and Pigments published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C11H21BF4N2O2, Formula: C20H28B2O4S2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Heeney, Martin published the artcileOrganic field effect transistors fabricated from polymerizable liquid crystals, Safety of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, the publication is Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) (2003), 44(2), 340-341, database is CAplus.

The synthesis and phase behavior of reactive mesogens based on phenylnaphthalene and quaterthiophenes are described. End groups compatible with free-radical polymerization were compared. The phase behavior was studied with DSC.

Polymer Preprints (American Chemical Society, Division of Polymer Chemistry) published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Safety of 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hassan Omar, Omar published the artcileSynthesis of D-glucose and L-phenylalanine substituted phenylene-thiophene oligomers, Computed Properties of 239075-02-6, the publication is Tetrahedron (2011), 67(2), 486-494, database is CAplus.

Phenylene-thiophene oligomers bearing peracetylated β-D-glucose or Boc-L-phenylalanine as chiral substituents were synthesized in good yields by a versatile protocol based on the Suzuki-Miyaura cross-coupling reaction. Aryl iodides bearing the chiral biomols. as substituents efficiently reacted with pinacol boronates of bi- or terthiophenes leading to the bio-functionalized oligomers in good yields.

Tetrahedron published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Computed Properties of 239075-02-6.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts