Materials having electron deficient moieties and methods of synthesizing thereof
AssigneeGeorgia Tech Research Corporation
InventorsSeth Marder, Junxiang Zhang
Life of this patent
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Abstract
Various materials and polymers having electron deficient moieties and methods of synthesizing thereof are described herein. Specifically, a C—H bond activation method is disclosed wherein an electron deficient group having one or more activated C—H bonds is coupled to one or more aryl groups to afford materials or polymers which may be used in organic electronic and photonic applications.
Claims14
A method comprising reacting a dicyanobenzodiimine with a first aryl group, in a first C—H activated coupling, wherein the dicyanobenzodiimine comprises the structure:
- wherein Y1 is selected from the group consisting of O, S, Se, NR1, and C(R1)═C(R1);
- R1 is independently selected at each occurrence from the group consisting of hydrogen, halogen, a C1-C30 alkyl group, a C1-C30 heteroalkyl group, a C5 -C10 heteroaryl group;
- and
- wherein a covalent bond is formed between the first aryl group and the dicyanobenzodiimine such that Hais substituted by the first aryl group;
- wherein the first aryl group has at least one labile bond and is selected from the following structures:
- wherein “- - -” denotes the bond which is formed between the first aryl group and the dicyanobenzodiimine;
- Y2 independently selected at each occurrence from the group consisting of O, S, Se, Ge, C(R1)2, Si(R1)2, Ge(R1)2, and NR1;
- R1 is independently selected at each occurrence from the group consisting of H, halogen, a C1-C30 alkyl group, a C1-C30 heteroalkyl group, a C5-C10 aryl group, and a C5-C10 heteroaryl group;
- R2 is independently selected at each occurrence from the group consisting of hydrogen, halogen, an alkyl group, a heteroalkyl group, a C5-C10 aryl group, and a C5-C10 heteroaryl group;
- and o has an integer value from 1-4;
- and
- wherein the reaction occurs in an organic solvent comprising a catalyst, a ligand, and a base.
A method comprising reacting a dicyanobenzodiimine with a first aryl group in a first C-H activated coupling, wherein the dicyanobenzodiimine comprises the structure:
- wherein Y1 is selected from the group consisting of O, S, Se, NR1, and C(R1)═C(R1);
- R1 is independently selected at each occurrence from the group consisting of hydrogen, halogen, an alkyl group, a heteroalkyl group, an aryl group, and a heteroaryl group;
- and
- wherein a covalent bond is formed between the first aryl group and the dicyanobenzodiimine such that Ha is substituted by the first aryl group;
- and
- further reacting the dicyanobenzodiimine with a second aryl group in a second C—H activated coupling, whereby a covalent bond is formed between the second aryl group and the dicyanobenzodiimine such that Hb is substituted with the second aryl group;
- wherein the first and second aryl groups each have at least one labile bond and are selected from the following structures:
- wherein “- - -” denotes the bond which is formed between the first aryl group and the dicyanobenzodiimine;
- Y2 independently selected at each occurrence from the group consisting of O, S, Se, Ge, C(R1)2, Si(R1)2, Ge(R1)2, and NR1;
- R1 is independently selected at each occurrence from the group consisting of hydrogen, halogen, a C1-C30 alkyl group, a C1-C30 heteroalkyl group, a C5-C10 aryl group, and a C5-C10 heteroaryl group;
- R2 is independently selected at each occurrence from the group consisting of hydrogen, halogen, a C1-C30 alkyl group, a C1-C30 heteroalkyl group, a C5-C10 aryl group, and a C5-C10 heteroaryl group;
- and o has an integer value from 1-4;
- and
- wherein the reaction occurs in an organic solvent comprising a catalyst, a ligand, and a base.
Dependencies are inferred from the claim text.