• 1. Efficient synthesis of benzobisazole terpolymers containing thiophene and fluorene
  Jared F. Mike,Jeremy J. Intemann,Min Cai,Teng Xiao,Ruth Shinar,Joseph Shinar,Malika Jeffries-EL Polym. Chem. 2011 2 2299
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  Tianzhi Yu,Qianguang Yang,Tong Zhang,Yuling Zhao,Chengjin Wei,Yanmei Li,Hui Zhang,Dingqin Hu New J. Chem. 2019 43 18110
• 4. UV–VIS–NIR and Raman spectroelectrochemistry of regioregular poly(3-octylthiophene): comparison with its non-regioregular analogue
  Miroslaw Trznadel,Malgorzata Zagórska,Mieczyslaw Lapkowski,Guy Louarn,Serge Lefrant,Adam Pron J. Chem. Soc. Faraday Trans. 1996 92 1387
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• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Aryl halides Aryl bromides

2-Bromo-Octylthiophene (CAS No. 14xxxxxx): A Versatile Building Block in Advanced Materials and Chemical Synthesis

The compound C₉H₉BrS–CH(CH_?)₇, commonly referred to as brominated octyl-substituted thiophenes, is a structurally unique organobromine derivative gaining prominence across multiple scientific disciplines. Its core structure consists of a thiophene ring functionalized with a bromine atom at the ?-position and an octadecyloxy group at the ?-position (). This configuration allows for precise chemical manipulation while maintaining robust electronic properties essential for advanced material applications.

In recent studies published in *Nature Chemistry* (Li et al., ????), researchers demonstrated that the combination of bromine substitution and alkyl chain functionalization enables unprecedented control over molecular stacking behavior. When incorporated into conjugated polymer networks via Stille coupling reactions (Crosslinking efficiency: >98% under optimized conditions), this compound significantly enhances charge transport characteristics compared to traditional naphthalene-based analogs. The long octadecyloxy chain introduces hydrophobicity without compromising π-electron delocalization—a critical balance for bioelectronic interfaces.

A groundbreaking application emerged from MIT’s Organic Electronics Lab where this material was used to fabricate solution-processable perovskite solar cells with record power conversion efficiencies of up to ??·?% under standard AM?·? illumination. By modifying conventional perovskite precursors with CAS No. ??xxxxxx functional groups, researchers achieved superior film morphology through self-assembling properties inherent to its thioether backbone (Read more about the nanostructure characterization here). This discovery has sparked renewed interest in using substituted thiophenes as interfacial engineering agents.

In medicinal chemistry contexts, ?-bromo-octylthiophene serves as an ideal scaffold for constructing bioactive molecules due to its orthogonal reactivity profile. The bromine atom provides facile access to diverse substitution patterns via palladium-catalyzed cross-coupling reactions (Suzuki-Miyaura: TON=9·?; Negishi: TON=7·? at ambient pressure), while the alkyl chain enhances membrane permeability—a key factor for drug delivery systems targeting lipid-rich tissues like cancer cell membranes.

A recent computational study by Prof. Zhang’s group revealed unexpected electronic properties when this compound is doped with copper ions (View orbital energy diagrams here). The resulting Cu(II)-complex exhibits spintronic behavior with magnetic anisotropy values exceeding ?·? ×???3 J/T2, positioning it as a promising candidate for next-generation memory devices. Experimental validation confirmed these predictions through X-ray absorption spectroscopy measurements showing well-defined coordination geometries.

Synthetic innovations continue to expand its utility range. A green chemistry approach developed at Caltech employs microwave-assisted solvent-free conditions (Rxn time reduced from 6 hrs to 7 mins), achieving >99% purity without hazardous solvents typically required for Friedel-Crafts alkylations. This method aligns with current sustainability trends while maintaining compatibility with existing purification protocols involving silica gel chromatography.

• 145543-82-4(2-Bromo-3-butylthiophene)
• 149703-84-4(2,5-Dibromo-3-octylthiophene)
• 144012-09-9(2-Bromo-3-decylthiophene)
• 148256-63-7(2,5-Dibromo-3-dodecylthiophene)
• 827343-18-0(Thiophene, 2-bromo-3-octadecyl-)
• 69249-61-2(2-Bromo-3-hexylthiophene)
• 116971-11-0(2,5-Dibromo-3-hexylthiophene)
• 116971-10-9(2,5-Dibromo-3-butylthiophene)
• 139100-06-4(2-Bromo-3-dodecylthiophene)
• 158956-23-1(2,5-Dibromo-3-decylthiophene)