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Description
TCI D4182 is 4,4'-Dihexyl-2,2'-bithiophene, an alkyl-substituted bithiophene isomer carrying hexyl chains at the 4 and 4' positions. As a heterocyclic building block, this compound serves as a core skeleton for constructing thiophene-based conjugated materials. Its role in the laboratory is to supply a bithiophene unit that is already well soluble in organic solvents while still retaining free alpha positions, so it is ready to be halogenated, borylated, or stannylated before moving on to subsequent cross-coupling and polymerization steps.
The distinguishing characteristic of this compound is the placement of the hexyl chains away from the inter-ring linkage. Unlike the 3,3' isomer, whose alkyl chains sit close to the connecting axis and introduce considerable steric hindrance, substitution at the 4 and 4' positions allows the two thiophene rings to remain relatively coplanar. This coplanarity matters because it supports better π-electron delocalization along the chain, giving a longer effective conjugation length, absorption at longer wavelengths, and a tendency toward more ordered molecular packing in thin films. At the same time, the hexyl chains provide the solubility needed for solution processing.
In Indonesian laboratories, this building block is typically used in organic electronics and materials chemistry research groups at universities and research institutes, as well as in synthetic laboratories preparing conjugated monomers and oligomers. It is generally handled at bench scale for functionalization and coupling work, where a soluble, reactive bithiophene precursor is needed as the starting point for building larger conjugated structures rather than being used as a finished material.
Laboratory Applications
- Conjugated polymer synthesis: the free alpha positions allow conversion into dihalide or diboronate monomers, making this a direct precursor for thiophene-based polymer backbones.
- Cross-coupling chemistry: after halogenation, borylation, or stannylation, the compound feeds into standard coupling sequences used to extend conjugation length in a controlled way.
- Organic electronic material development: the coplanar ring arrangement supports π-delocalization and ordered thin-film packing, which are the properties targeted in semiconducting material research.
- Oligothiophene preparation: the intact bithiophene core provides two rings at once, shortening the route to longer oligomers compared with building up from single thiophene units.
- Solution-processed film studies: the hexyl chains give solubility in organic solvents, allowing the material and its derivatives to be deposited from solution for thin-film characterization.
Specifications
- Brand: TCI
- CAS number: 135926-94-2
- Chemical name: 4,4'-Dihexyl-2,2'-bithiophene
- Category: Chemistry > Building Blocks > Heterocyclic Building Blocks
- Pack sizes: available in the catalogue pack sizes offered by TCI for this item
- Storage: keep in a cool, dry place in the tightly closed original container
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from heat sources, direct sunlight, and strong oxidizing agents. Keep the material in its original supplier container or in a compatible amber glass container to limit exposure to light and moisture, and label any transferred portions clearly. Handle in a fume hood using nitrile gloves, safety glasses, and a laboratory coat, and avoid inhalation of vapors or dust and direct contact with skin and eyes. For air- or moisture-sensitive work, transfer under an inert atmosphere. Consult the manufacturer's safety data sheet before use and dispose of residues as chemical waste according to institutional procedures.
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