3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene

Name: 3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene
SKU: ACM850881093-1
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Catalog NumberACM850881093-1

CAS Number850881-09-3

CategorySmall Molecule Semiconductor Building Blocks; Electroluminescence Materials; Polymers; Semiconductor Blocks

3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene

IUPAC Name

2-(3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Molecular Weight

294.3g/mol

Molecular Formula

C16H27BO2S

Canonical SMILES

B1(OC(C(O1)(C)C)(C)C)C2=C(C=CS2)CCCCCC

InChI

InChI=1S/C16H27BO2S/c1-6-7-8-9-10-13-11-12-20-14(13)17-18-15(2,3)16(4,5)19-17/h11-12H,6-10H2,1-5H3

InChI Key

XCXAUPBHQCCWCI-UHFFFAOYSA-N

Application

The purpose of 3-Hexyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene is to serve as a versatile reagent in the synthesis of advanced materials for optoelectronic applications. By facilitating Suzuki-Miyaura cross-coupling reactions, this compound plays a critical role in the production of p-type or n-type switching ambipolar polymers, particularly those based on bithiazole-benzothiadiazole, which are utilized in solar cell technology. Additionally, it supports the hierarchical self-assembly of semiconductor-functionalized peptide alpha-helices, enhancing their optoelectronic properties. This reagent is essential in crafting photovoltaic materials, polymers, and thiophene-based compounds, all of which possess significant photophysical, electrochemical, and fluorescent characteristics. Its use extends to the development of polymer solar cells, focusing on low band gap poly(1,4-arylene-2,5-thienylene)s with benzothiadiazole units, and it is also involved in the synthesis of dithienothiophene-based dyes for dye-sensitized solar cells, thereby underscoring its importance in cutting-edge solar technology advancements.

Complexity

304

Covalently-Bonded Unit Count

Exact Mass

294.182481g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

294.182481g/mol

Rotatable Bond Count

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