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2,2'-Bithiophene is used as a precursor in the preparation of 5,5'-bis(trimethylstannyl)-2,2'-bithiophene , which is used for the synthesis of small molecules and polymer semiconductors for organic field-effect transistor (OFETs), organic light-emitting diode (OLED), Plastic Light Emitting Diode (PLED) and Organic Photovoltaic (OPV) applications. It is associated with aryl iodides and involved in rhodium catalyzed arylation of heteroarenes.
Can be converted to its 5-lithio- and 5,5'-dilithio derivatives by PhLi and n-BuLi respectively. Chemistry of this type has found applications in synthesis of: liquid crystal molecules: Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 218, 113 (1992); bithienoquinoid compounds as electron donors for organic conductors: Tetrahedron Lett., 33, 5405 (1992); conjugated thiophene oligomers as organic semiconductors: J. Am. Chem. Soc., 115, 8716 (1993); polythiophenes as conducting polymers: Synth. Met., 55, 420 (1993).
Gao, H.; Cheng, H.; Yang, Z.; Prehm, M.; Cheng, X.; Tschierske, C. Synthesis and self-assembly of 5,5'-bis(phenylethynyl)-2,2'-bithiophene-based bolapolyphiles in triangular and square LC honeycombs. J. Mater. Chem. C 2015, 3 (6), 1301-1308.
Pace, G.; Caranzi, L.; Bucella, S. G.; Canesi, E. V.; Dell'Erba, G.; Bertarelli, C.; Caironi, M. Electronic transport regimes through an alkoxythiolated diphenyl-2,2'-bithiophene-based molecular junction diodes: critical assessment of the thermal dependence. Nanoscale 2015, 7 (5), 2076-2084.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant