Abstract: Multilayer organic electronic devices having an electron transport layer (ETL). The ETL is a film comprising an N-annulated perylene diimide (NPDI) compound having at least one pyrrole N—H bond and at least 1 equivalent of Cs2CO3 with respect to the NPDI compound and the number of pyrrolic N—H bonds in the NPDI compound. The ETL is positioned between the photoactive layer and the top electrode (cathode). Multilayer devices including the ETL are fabricated employing immiscible solvent methods. A method for making the ETL layers is provided which employs an ink formulation in which the NPDI compound is solubilized in a selected polar solvent by addition of at least one equivalent of Cs2CO3 respect to the NPDI compound. Exemplary polar solvents include ethanol, 1-propanol, ethyl acetate and mixtures thereof.

Abstract: Organic photovoltaics (OPVs) based on a slot-die coated ternary blends for low-intensity light harvesting are disclosed herein. The ternary blends comprise either a N-annulated perylene diimide-based electron acceptor material or an aalkyl-12,13-dihydro[1,2,5] thiadiazolo[3,4e]thieno[2?,3?:4?,5] thieno[2?,3?:4,5] pyrrolo[3,2-g] thieno [2?,3?:4,5]thieno [3,2-b]indole-2,10-diyl)bis(methanylylidene)) bis(3-oxo-2,3-dihydro1Hindene-2,1-diylidene))dimalononitrile) (BTP)-based electron acceptor material, a second acceptor material, and an electron donor material which comprises poly[(2,5-bis(2-hexyldecyloxy) phenylene)-alt-(5,6-difluoro-4,7-di(thiophen-2-yl)benzo[c] [1,2,5]thiadiazole)] (PPDT2FBT). In an aspect, a N-annulated perylene diimide dimer (tPDI2N-EH, PDI) acceptor material was incorporated into a blend of donor polymer material (PPDT2FBT) and fullerene acceptor [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) material to give ternary bulk heterojunction (BHJ) blends.

Abstract: Thin films of organic semiconducting material comprising perylene diimide small molecules with pyrrolic N—H bonds. Films are prepared using green solvents including water and alcohols. The films can be solvent-resistant and generally range in thickness from 10 to 1000 nm. Perylene diimide molecules are dissolved in solvent by addition of a base to polarize the pyrrolic N—H bond believed to generate an ionic salt in alcohol or aqueous solution. Devices containing such films are provided. Methods of making films and methods of using films in OPV device applications and in amine sensors are provided.

Abstract: Oligomeric compounds useful as organic conjugated materials in electronic devices. Oligomeric compounds contain three or more or four or more of certain PDI units bonded to an organic core. The organic core contains one, two or more thiophene rings. The organic core can contain two or more thiophene rings separated by a linker group; two or more thiophene rings directly fused to each other or indirectly fused to each other through an optionally substituted aromatic or non-aromatic carbocylic ring system or an optionally substituted aromatic heterocyclic or non-aromatic heterocyclic ring system; or each of two or more thiophene rings is fused to an aromatic or non-aromatic carbocylic ring system or an aromatic heterocyclic or non-aromatic heterocyclic ring system and the resulting fused rings containing a thiophene ring are each separated by a linker group M. Methods for making oligomeric compounds by direct heteroarylation are provided.

Abstract: Small organic molecule semi-conducting chromophores containing a pyridalthiadiazole, pyridaloxadiazole, or pyridaltriazole core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Abstract: Oligomeric compounds useful as organic conjugated materials in electronic devices. Oligomeric compounds contain three or more or four or more of certain PDI units bonded to an organic core. The organic core contains one, two or more thiophene rings. The organic core can contain two or more thiophene rings separated by a linker group; two or more thiophene rings directly fused to each other or indirectly fused to each other through an optionally substituted aromatic or non-aromatic carbocylic ring system or an optionally substituted aromatic heterocyclic or non-aromatic heterocyclic ring system; or each of two or more thiophene rings is fused to an aromatic or non-aromatic carbocylic ring system or an aromatic heterocyclic or non-aromatic heterocyclic ring system and the resulting fused rings containing a thiophene ring are each separated by a linker group M. Methods for making oligomeric compounds by direct heteroarylation are provided.

Abstract: PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.

Abstract: Oligomeric compounds useful as organic conjugated materials in electronic devices. Oligomeric compounds contain three or more or four or more of certain PDI units bonded to an organic core. The organic core contains one, two or more thiophene rings. The organic core can contain two or more thiophene rings separated by a linker group; two or more thiophene rings directly fused to each other or indirectly fused to each other through an optionally substituted aromatic or non-aromatic carbocylic ring system or an optionally substituted aromatic heterocyclic or non-aromatic heterocyclic ring system; or each of two or more thiophene rings is fused to an aromatic or non-aromatic carbocylic ring system or an aromatic heterocyclic or non-aromatic heterocyclic ring system and the resulting fused rings containing a thiophene ring are each separated by a linker group M. Methods for making oligomeric compounds by direct heteroarylation are provided.

Abstract: Oligomeric compounds useful as organic conjugated materials in electronic devices. Oligomeric compounds contain three or more or four or more of certain PDI units bonded to an organic core. The organic core contains one, two or more thiophene rings. The organic core can contain two or more thiophene rings separated by a linker group; two or more thiophene rings directly fused to each other or indirectly fused to each other through an optionally substituted aromatic or non-aromatic carbocylic ring system or an optionally substituted aromatic heterocyclic or non-aromatic heterocyclic ring system; or each of two or more thiophene rings is fused to an aromatic or non-aromatic carbocylic ring system or an aromatic heterocyclic or non-aromatic heterocyclic ring system and the resulting fused rings containing a thiophene ring are each separated by a linker group M. Methods for making oligomeric compounds by direct heteroarylation are provided.

Abstract: A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b?]dithiophene or organotin-functionalized indaceno[2,1-b:3,4-b?]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

Abstract: PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.

Abstract: Small organic molecule semi-conducting chromophores containing a pyridalthiadiazole, pyridaloxadiazole, or pyridaltriazole core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Abstract: Small organic molecule semi-conducting chromophores containing a pyridalthiadiazole, pyridaloxadiazole, or pyridaltriazole core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Abstract: PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.

Abstract: PDI derivatives useful as opto-electronically active materials or for the synthesis of such materials. Certain compounds herein function as efficient electron acceptors and are useful as electron active components of electronic devices.

Abstract: A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b?]dithiophene or organotin-functionalized indaceno[1,2-b:5,6-b?]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

Abstract: Small organic molecule semi-conducting chromophores containing a pyridalthiadiazole, pyridaloxadiazole, or pyridaltriazole core structure are disclosed. Such compounds can be used in organic heterojunction devices, such as organic small molecule solar cells and transistors.

Abstract: A method of regioselectively preparing a pyridine-containing compound is provided. In particular embodiments, the method includes reacting halogen-functionalized pyridal[2,1,3]thiadiazole with organotin-functionalized cyclopenta[2,1-b:3,4-b?]dithiophene or organotin-functionalized indaceno[2,1-b:3,4-b?]dithiophene. Also provided is a method of preparing a polymer. The method includes regioselectively preparing a monomer that includes a pyridal[2,1,3]thiadiazole unit; and reacting the monomer to produce a polymer that includes a regioregular conjugated backbone section, wherein the section includes a repeat unit containing the pyridal[2,1,3]thiadiazole unit. A polymer that includes a regioregular conjugated backbone section, and electronic devices that include the polymer, are also provided.

Abstract: A compound having the formula (I) where each of R1, R2, R3 and R4 is independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C16-C20 linear alkyl-, RO—, —NRR?, —PRR?, —SR, fluoro substituted forms thereof, and perfluoro forms thereof: and R5 is C6-C18 aryl-, C3-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C3-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; where R and R? are each independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; A is N, P, S, or O with the proviso that when A is S, R2 is a nullity; and M is

Abstract: A compound having the formula (I) where each of R1, R2, R3 and R4 is independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl s?bstituent, C4-C20 branched alkyl-, C16-C20 linear alkyl-, RO—, —NRR?, —PRR?, —SR, fluoro substituted forms thereof, and perfluoro forms thereof: and R5 is C6-C18 aryl-, C5-C8cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C3-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; where R and R? are each independently C6-C18 aryl-, C5 -C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; A is N, P, S, or O with the proviso that when A is S, R2 is a nullity; and M is