Novel dihydropyrrolo[2,3-f] indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof

A compound of formula:

• wherein Ar is an optionally substituted aromatic or heteroaromatic group or conjugated group;
• k is an integer from 0 to 5 with the proviso that when k is 0, the structure results in a direct bond between the thiophene and pyrrole group;
• each X is independently NR1, PR1, AsR1, Sb, O, S, Te, or Se, with the proviso that due to conjugation, X may be bonded to one or more additional R1;
• each Y is independently H, halo, trialkylsilane, optionally substituted C1-C40 alkyl, optionally substituted aralkyl, alkoxy, alkylthio, optionally substituted C2-C40 alkenyl, optionally substituted C2-C40 alkynyl, aminocarbonyl, acylamino, acyloxy, aryl, aryloxy, optionally substituted amino, carboxyalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, halo, acyl, optionally substituted heteroaryl, optionally substituted heteroaralkyl, heteroaryloxy, optionally substituted heterocyclyl, thiol, alkylthio, heteroarylthiol, optionally substituted sulfoxide, optionally substituted sulfone, OSO-alkyl, Mg-halo, Zn-halo, Sn(alkyl)3, SnH3, B(OH)2, B(alkoxy)2, or OTs;
• and each R, R1, R2, and R3 is independently H, halo, optionally substituted C1-C40 alkyl, optionally substituted aralkyl, alkoxy, alkylthio, optionally substituted C2-C40 alkenyl, optionally substituted C2-C40 alkynyl, aminocarbonyl, acylamino, acyloxy, optionally substituted aryl, aryloxy, optionally substituted amino, carboxyalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, acyl, optionally substituted heteroaryl, optionally substituted heteroaralkyl, heteroaryloxy, optionally substituted heterocyclyl, thiol, alkylthio, heteroarylthiol, optionally substituted sulfoxide, or optionally substituted sulfone.