Abstract
AbstractCyclopentadithiophene (CPDT), a Csp3-bridged bithiophene heteroaromatic unit, displays interesting properties when it is embedded in the repeating units of π-conjugated polymers, and they are applied in organic electronics devices. Common synthetic routes to CPDT-derived polymers rely on toxic methodologies whilst alternative non-toxic strategies such as the Suzuki-Miyaura reaction have been less studied. In this report we demonstrate that the use of a N-methyliminodiacetic acid (MIDA) boronate ester-derived CPDT monomer allows the efficient formation of poly(cyclopentadithiophene) homopolymer under Suzuki-Miyaura cross-coupling reaction conditions. Thus, the use of MIDA boronate esters might be extended to other organic units to design and construct a plethora of π-conjugated polymers.
Highlights
Introduction π-conjugated polymers are important materials for organic electronic applications, and thienyl-derived moieties possess excellent electronic properties
The Direct C-H Electrophilic Borylation synthetic methodology (Bagutski et al, 2013) was employed for the preparation of the methyliminodiacetic acid (MIDA) boronate ester monomer, 1, according to the procedure previously reported (Ayuso Carrillo et al, 2015). pCPDT homopolymer was prepared via Suzuki-Miyaura polymerisation methodology (Suzuki, 2011)
Further details are provided in the Supplementary Materials
Summary
PCPDT, via Suzuki-Miyaura polymerisation using MIDA boronate esters as the key boron masking group in AB-type monomers, and demonstrate their potential as efficient substrates for the formation of thienyl-derived conjugated polymers in high yields and high polymer molecular weights
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