Boron ester fused thiophene monomers
A compound of formula (I), formula (II), or a combination thereof, and salts thereof is described. Each A may be independently an optionally substituted conjugated species or an optionally substituted aromatic species. Each R may be independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, or H. Each R 2 may be independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, H, or part of a cyclic boronate ester with an other R 2 . Each n may be independently less than or equal to 3 and greater than or equal to 1. Each x may be independently less than or equal to 3.
1. A method of making a compound of formula (I) and salts thereof,
the method comprising:
reacting a compound of formula (III)
with an alkyl lithium to give an intermediate; and
reacting the intermediate with a compound of formula (IV)
to give the compound of formula (I),
wherein each A is independently an optionally substituted conjugated species or an optionally substituted aromatic species,
wherein each R and R 3 is independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, or H,
wherein each R 2 is independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, H, or part of a cyclic boronate ester with another R 2 ,
wherein each n is independently less than or equal to 3 and greater than or equal to 1, and
wherein each x is independently less than or equal to 3.
2. The method of claim 1 , wherein each x is independently less than or equal to 1.
3. A method of making a compound of formula (II) and salts thereof,
the method comprising:
reacting a compound of formula (V)
with an alkyl lithium to give an intermediate; and
reacting the intermediate with a compound of formula (IV)
to give the compound of formula (II),
wherein each A is independently an optionally substituted conjugated species or an optionally substituted aromatic species,
wherein each R and R 3 is independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, or H,
wherein each R 2 is independently an optionally substituted C 1 -C 40 linear alkyl chain, an optionally substituted branched alkyl chain, an optionally substituted alkyl chain containing heteroatoms, substituted alkyl chains, H, or part of a cyclic boronate ester with another R 2 ,
wherein each n is independently less than or equal to 3 and greater than or equal to 1, and
wherein each x is independently less than or equal to 3.
4. The method of claim 3 , wherein each x is independently less than or equal to 1.