• 3,6-Dibromothieno[3,2-b]thiophene (CAS 392662-65-6) - TCI D3679 - AMI Scientific
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CAS 392662-65-6

3,6-Dibromothieno[3,2-b]thiophene TCI D3679

3,6-Dibromothieno[3,2-b]thiophene TCI D3679
Rp 1.888.950,00
Rp 1.888.950,00
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TCI D3679 3,6-Dibromothieno[3,2-b]thiophene is a semiconductor material building block built around a fused thienothiophene core, the same rigid framework found in its 2,5-isomer, but with the bromine atoms placed at the 3 and 6 positions — the beta positions on each of the two thiophene rings. This shift in substituent location changes the direction in which the molecule grows during coupling and alters the conjugation pattern that forms, which gives the compound a distinct role in materials design. In the laboratory, it is used to attach side groups or functional units to the lateral edges of the thienothiophene skeleton while deliberately leaving the alpha positions free for functionalisation at a later synthetic stage.

The characteristic that makes researchers select this isomer is the synthetic flexibility that beta substitution offers. With the 2 and 5 positions left open, chemists can first install alkyl side chains or electron-withdrawing groups at positions 3 and 6 to tune solubility, solid-state packing and orbital energy levels, and only afterwards carry out halogenation or coupling at the alpha positions to build the polymer chain. This stepwise approach matters because solubility and thin-film morphology strongly determine how a conjugated material behaves once it is processed, and controlling them early in the sequence is easier than correcting them at the end. The fused, planar core is retained throughout, so the electronic backbone stays intact while the peripheral chemistry is adjusted.

In Indonesian laboratories, this building block is typically found in university and institutional research groups working on organic electronics, conjugated polymers and functional materials, where multi-step synthesis routes are planned around a well-defined halogenated core. It is generally handled in small-scale synthetic work on a Schlenk line or in an inert-atmosphere setup, purified and characterised in-house, and then carried forward into cross-coupling chemistry. Groups building device-oriented materials value having a defined starting point rather than preparing the dibrominated core themselves.

  • Conjugated polymer synthesis — the two bromine handles allow controlled chain extension through metal-catalysed cross-coupling, while the fused thienothiophene core contributes rigidity and extended conjugation to the resulting backbone.
  • Side-chain engineering studies — installing alkyl chains at the beta positions lets researchers tune solubility and solid-state packing before the alpha positions are used for polymerisation, separating processability from backbone construction.
  • Organic semiconductor material development — the planar fused core and defined substitution pattern make it a reliable starting point for building small molecules and oligomers intended for charge-transport measurements.
  • Frontier orbital level tuning — attaching electron-withdrawing groups at positions 3 and 6 provides a direct route to adjusting orbital energy levels of the final material without disturbing the alpha reactive sites.
  • Isomer comparison research — pairing this beta-substituted compound with the 2,5-isomer lets groups study how substitution position alone changes conjugation pathways, molecular growth direction and resulting film behaviour.

Brand TCI
CAS number 392662-65-6
Molecular formula —
Purity —
Category Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes available in standard TCI research-scale packaging; please confirm the pack size required when ordering
Physical form —
Storage keep in the original tightly closed container, protected from light and moisture, as directed on the manufacturer's label
  • Chemical name: 3,6-Dibromothieno[3,2-b]thiophene

Store the material in its original tightly closed container in a cool, dry and well-ventilated place, protected from light and away from moisture, following the storage conditions stated on the manufacturer's label and Safety Data Sheet. Amber glass or the supplied container is preferred, and transfers are best carried out under an inert atmosphere where the subsequent chemistry requires dry conditions. Handle the compound inside a fume hood using nitrile gloves, safety goggles and a laboratory coat, avoid generating dust during weighing, and keep it separated from strong oxidising agents. Close the container promptly after use and dispose of residues and contaminated consumables through the institution's chemical waste stream. Always consult the Safety Data Sheet before first use.

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