Near infrared dyes for biological imaging and optoelectronic devices

A near infrared dye comprising a counterion and a structure of Formula I

• wherein X is selected from O, Si and P;
• R is selected from hydrogen, —C(O)OH,
• a substituted or unsubstituted linear or branched C1-C18 alkyl group,
• a substituted or unsubstituted linear or branched C2-C18 alkenyl group,
• a substituted or unsubstituted C3-C10 cycloalkyl group,
• a substituted or unsubstituted linear or branched C1-C18 alkoxy group,
• an ester group represented by the formula —C(O)OA1, wherein A1 is a substituted or unsubstituted linear or branched C1-C18 alkyl group, a substituted or unsubstituted linear or branched C2-C18 alkenyl group or a substituted or unsubstituted C3-C10 cycloalkyl group,
• an amide group represented by the formula —C(O)N(A2)2, wherein A2 is selected from a substituted or unsubstituted linear or branched C1-C18 alkyl group, a substituted or unsubstituted linear or branched C2-C18 alkenyl group, or a substituted or unsubstituted C3-C10 cycloalkyl group, or
• an ether group represented by the formula —CH2OA3 wherein A3 is selected from a substituted or unsubstituted linear or branched C1-C18 alkyl group, a substituted or unsubstituted linear or branched C2-C18 alkenyl group, or a or a substituted or unsubstituted C3-C10 cycloalkyl group;
• when X is O, then R3 and R4 are absent, and
• when X is Si, then R3 and R4 are each singly bonded to the Si atom, and are independently selected from hydrogen, a substituted or unsubstituted C1-C18 linear or branched alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group,
• when X is P, then R3 is singly bonded to the P atom and is selected from hydrogen, a substituted or unsubstituted C1-C18 linear or branched alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group is P, and R4 is singly bonded to the P and is a substituted or unsubstituted C1-C18 linear or branched alkyl group or a substituted or unsubstituted C3-C10 cycloalkyl group or R4 is doubly bonded to the P and is an oxygen;
• wherein R19, R20, R22, R23, R24, R25, R26, R27, R28, and R29 are each independently selected from hydrogen, sulfonate, halogen, hydroxy, amino, nitro, cyano, carboxy, an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, a heterocyclic group having 3 to 16 carbon atoms, an alkylether having 2 to 20 carbon atoms and 1 to 5 oxygen atoms, and an alkoxy group having 1 to 20 carbon atoms or wherein one or more pair of R22 and R23, R24 and R25, R25 and R26, R26 and R27, R27 and R28, R28 and R29, together with the carbons they are attached form a saturated or unsaturated 6 membered ring;
• and
• R1 and R2 are both selected from one of the following Groups A, B and C:
• Group A
• R1 is hydrogen and R2 is a donor which is substituted or unsubstituted and is a 1-(thiophen-2-yl)piperidine, 1-(thieno[3,2-b]thiophen-2-yl)piperidine or 1-([2,2′-bithiophen]-5-yl)piperidine;
• or
• Group B
• both R1 and R2 are the same donors and both are substituted or unsubstituted, and are selected from 1-(thiophen-2-yl)piperidine, 1-(thieno[3,2-b]thiophen-2-yl)piperidine, and 1-([2,2′-bithiophen]-5-yl)piperidine;
• or
• Group C
• R1 and R2 are different donors and R1 is a donor which is substituted or unsubstituted and is a 1-(thiophen-2-yl)piperidine, 1-(thieno[3,2-b]thiophen-2-yl)piperidine or 1-([2,2′-bithiophen]-5-yl)piperidine and R2 is a donor which is substituted or unsubstituted and is selected from 1-(thiophen-2-yl)piperidine, 1-(thieno[3,2-b]thiophen-2-yl)piperidine, 1-([2,2′-bithiophen]-5-yl)piperidine, C2-C12 dialkyl amino, indolizine-3-yl, diphenylamino, and julolidinyl.