Compositions and methods of promoting organic photocatalysis
AssigneesThe Regents of the University of Colorado, Colorado State University Research Foundation
InventorsGarret Miyake, Jordan Corinne Theriot, Matthew D. Ryan, Ryan Michael Pearson, Tracy Allen French, Haishen Yang, Andrew Lockwood, Charles Musgrave, Chern-Hooi Lim, Ya Du, Blaine McCarthy
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Abstract
The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
Claims38
A method of promoting reaction of at least one reagent, the method comprising:
- irradiating with electromagnetic radiation the at least one reagent in the presence of an organic compound, or a salt or solvate thereof, selected from the group consisting of:
- wherein:
- each occurrence of R is independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, optionally substituted phenyl, —OH, —O(C1-C6 alkyl), —NO2, —CN, —C(═O)OH, —C(═O)O(C1-C6 alkyl), —C(═O)O-phenyl, —C(═O)(C1-C6 alkyl), —C(═O)-phenyl, —S(O)2NH2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)(C1-C6 alkyl), —S(C1-C6 alkyl), —S(O) (C1-C6 alkyl), —S(O)2(C1-C6 alkyl), —S(phenyl), —S(O)(phenyl), and —S(O)2(phenyl),
- each occurrence of R1 is independently selected from the group consisting of phenyl, 1-naphthyl, and 2-naphthyl, each of which is independently substituted with at least one R;
- each occurrence of R2 and R3 is independently selected from the group consisting of phenyl and 4-phenyl-phenyl, each of which is independently substituted with at least one R;
- and
- each occurrence of R4, R5 R6, and R7 is independently selected from the group consisting of phenyl, 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, triphenylamino, phenanthrenyl, and pyrenyl, each of which is independently substituted with at least one R,
- wherein:
- if the compound is
- then
- each occurrence of R is independently selected from the group consisting of C2-C6 alkyl, C1-C6 haloalkyl, substituted phenyl, —O(C2-C6 alkyl), —NO2, —C(═O)OH, —C(═O)O(C2-C6 alkyl), —C(═O)O-phenyl, —C(═O)(C1-C6 alkyl), —C(═O)-phenyl, —S(O)2NH2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)(C1-C6 alkyl), —S(C1-C6 alkyl), —S(O) (C1-C6 alkyl), —S(O)2(C1-C6 alkyl), —S(phenyl), —S(O)(phenyl), and —S(O)2(phenyl);
- if the compound is
- then
- each occurrence of R is independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, optionally substituted phenyl, —OH, —O(C2-C6 alkyl), —NO2, —CN, —C(═O)OH, —C(═O)O(C1-C6 alkyl), —C(═O)O-phenyl, —C(═O)(C1-C6 alkyl), —C(═O)-phenyl, —S(O)2NH2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)(C1-C6 alkyl), —S(C1-C6 alkyl), —S(O) (C1-C6 alkyl), —S(O)2(C1-C6 alkyl), —S(phenyl), —S(O)(phenyl), and —S(O)2(phenyl);
- if the compound is
- then
- each occurrence of R1 is independently selected from the group consisting of 1-naphthyl and 2-naphthyl, each of which is independently substituted with at least one R.
A method of promoting reaction of at least one reagent, the method comprising:
- irradiating with electromagnetic radiation the at least one reagent in the presence of an organic compound, or a salt or solvate thereof, selected from the group consisting of:
- wherein:
- each occurrence of R is independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, optionally substituted phenyl, —OH, —O(C1-C6 alkyl), —NO2, —CN, —C(═O)OH, —C(═O)O(C1-C6 alkyl), —C(═O)O-phenyl, —C(═O)(C1-C6 alkyl), —C(═O)-phenyl, —S(O)2NH2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)(C1-C6 alkyl), —S(C1-C6 alkyl), —S(O) (C1-C6 alkyl), —S(O)2(C1-C6 alkyl), —S(phenyl), —S(O)(phenyl), and —S(O)2(phenyl),
- each occurrence of R1 is independently selected from the group consisting of phenyl, 1-naphthyl, and 2-naphthyl, each of which is independently substituted with at least one R;
- each occurrence of R2 and R3 is independently selected from the group consisting of phenyl and 4-phenyl-phenyl, each of which is independently substituted with at least one R;
- and
- each occurrence of R4, R5 R6, and R7 is independently selected from the group consisting of phenyl, 4-phenyl-phenyl, 1-naphthyl, 2-naphthyl, triphenylamino, phenanthrenyl, and pyrenyl, each of which is independently substituted with at least one R.
A method of promoting reaction of at least one reagent, the method comprising:
- irradiating with electromagnetic radiation the at least one reagent in the presence of an organic compound, or a salt or solvate thereof, selected from the group consisting of:
- wherein R is independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 haloalkyl, optionally substituted phenyl, —OH, —O(C1-C6 alkyl), —NO2, —CN, —C(═O)OH, —C(═O)O(C1-C6 alkyl), —C(═O)O-phenyl, —C(═O)(C1-C6 alkyl), —C(═O)-phenyl, —S(O)2NH2, —S(O)2NH(C1-C6 alkyl), —S(O)2N(C1-C6 alkyl)(C1-C6 alkyl), —S(C1-C6 alkyl), —S(O) (C1-C6 alkyl), —S(O)2(C1-C6 alkyl), —S(phenyl), —S(O)(phenyl), and —S(O)2(phenyl).
Dependencies are inferred from the claim text.