US 11,685,743 B2
Open-shell pi-conjugated molecules exhibiting multidimensional intermolecular covalency, compositions and process for preparing
Mark Chen, Bethlehem, PA (US); Caleb Wehrmann, Bethlehem, PA (US); and Ryan Charlton, Collegeville, PA (US)
Assigned to Lehigh University
Appl. No. 17/57,488
Filed by Lehigh University, Bethlehem, PA (US)
PCT Filed May 21, 2019, PCT No. PCT/US2019/033361
§ 371(c)(1), (2) Date Nov. 20, 2020,
PCT Pub. No. WO2019/226678, PCT Pub. Date Nov. 28, 2019.
Claims priority of provisional application 62/674,480, filed on May 21, 2018.
Prior Publication US 2021/0363153 A1, Nov. 25, 2021
Int. Cl. C07D 493/06 (2006.01); C07D 471/06 (2006.01)
CPC C07D 493/06 (2013.01) [C07D 471/06 (2013.01)] 12 Claims
 
1. A compound having the formula:

OG Complex Work Unit Chemistry
wherein R is chosen from substituted or unsubstituted phenyl, said substitutions are independently chosen from:
i) OR1, wherein R1 is selected from hydrogen, substituted or unsubstituted C1-C18 linear, branched or cyclic alkyl, and substituted or unsubstituted phenyl, said substitutions are selected from hydroxyl, C1-C18 linear, branched or cyclic alkyl, and combinations thereof;
ii) NR2R2, wherein each R2 is independently selected from hydrogen and C1-C4 linear, branched or cyclic alkyl;
iii) substituted or unsubstituted C1-C18 linear, branched or cyclic alkyl, said substitutions are selected from hydroxyl, C1-C8 linear, branched or cyclic alkyl, phenyl, and combinations thereof;
iv) substituted or unsubstituted aryl chosen from phenyl, naphthyl, phenanthrenyl, or fluorenyl; and
v) substituted or unsubstituted heteroaryl;
wherein A has the formula chosen from:

OG Complex Work Unit Chemistry
iv) combinations thereof;
each R4 is independently chosen from:
i) OR5, wherein R5 is selected from hydrogen, substituted or unsubstituted C1-C18 linear, branched or cyclic alkyl, and substituted or unsubstituted phenyl, said substitutions are selected from hydroxyl, C1-C4 linear, branched or cyclic alkyl, and combinations thereof;
ii) NR6R6, wherein each R6 is independently chosen from hydrogen, C1-C4 linear, branched or cyclic alkyl;
iii) hydrogen, substituted or unsubstituted C1-C18 linear, branched or cyclic alkyl, said substitutions are selected from hydroxyl, C1-C4 linear, branched or cyclic alkyl, phenyl, and combinations thereof; or
iv) a polyethylene glycol unit having the formula:
—O(CH2CH2O)nR7
R7 is hydrogen or C1-C4 alkyl, the index n is from about 5 to about 500;
each Y is independently chosen from O, N, S, P, SO, SO2, PO, NO, NR3, or C(R8)2; each R8 is independently chosen from:
i) OR9, wherein R9 is chosen from hydrogen, substituted or unsubstituted C1-C4 linear, branched or cyclic alkyl, and substituted or unsubstituted phenyl, said substitutions are chosen from hydroxyl, C1-C4 linear, branched or cyclic alkyl, and combinations thereof;
ii) NR10R10, wherein each R10 is independently selected from hydrogen and C1-C4 linear, branched or cyclic alkyl; or
iii) substituted or unsubstituted C1-C6 linear, branched or cyclic alkyl, said substitutions are chosen from hydroxyl, C1-C4 linear, branched or cyclic alkyl, phenyl, and combinations thereof; and
each X is an anion independently chosen from halogen, BF4−, ClO4−, triflate, mesylate, tosylate, and combinations thereof.