# US 7,408,058 B2 · Regioisomerically pure oxochlorins and methods of synthesis

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- Number: US 7,408,058 B2
- Document ID: US7408058B2
- Status: Granted
- Kind: B2
- Application number: 10/760,968
- Filed: 2004-01-20
- Published: 2004-08-05
- Granted: 2008-08-05
- Earliest claimed: 2000-07-21
- Assignees: North Carolina State University
- Inventors: Jonathan S. Lindsey; Masahiko Taniguchi; Sreedharan Prathapan; Han-Je Kim; Man Nyoung Kim
- Web page: https://patentgrep.com/patent/US7408058B2

## CPC

- C07D 487/22: in which the condensed system contains four or more hetero rings
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C09B 47/00: Porphines; Azaporphines {(non-dyeing compounds C07D487/22)}
- C09B 69/109: {containing other specific dyes}
- H01G 9/2059: {comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution}
- H01G 9/209: {Light trapping arrangements}
- H10K 85/361: {Polynuclear complexes, i.e. complexes comprising two or more metal centers}
- H10K 10/701: {Organic molecular electronic devices}
- H10K 85/30: Coordination compounds
- Y02E 10/542: Dye sensitized solar cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- H01G: CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE (selection of specified materials as dielectric H01B3/00; capacitors having potential barriers H10D1/62, H10K10/10)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method of making an oxochlorin comprises the steps of oxidizing a chlorin to produce a mixture of hydronchlorin and oxochlorin, and then oxidizing the hydroxychlorin in said mixture, preferably with DDQ, to produce a mixture consisting essentially of oxochlorin. The step of oxidizing a chlorin is carried out by exposing the chlorin to alumina, typically in the presence of an oxidizing agent such as air or alumina. The oxidizing steps may be carried out in an organic solvent such as toluene. The chlorin is preferably a C-methylated chlorin, and is preferably metalated.

## Claims

### Claim 1

A trans substituted oxochlorin compound of Formula X:
wherein:
M is a metal selected from the group consisting of Zn, Mg, Pt, Pd, Sn and Al;
K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, Se, Te, and CH;
S1, S2, S3, S4, S5, S6, S8, S9, S10, S11, S12, and S14 are independently selected from the group consisting of H, aryl, phenyl, alkyl, cycloalkyl, spiroalkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
wherein S7 and S13 are together ═O;
and wherein either (i) S1 and S5 are trans-substituted linking groups Q1 and Q2, (ii) S2 and S6 are trans-substituted linking groups Q1 and Q2, (iii) S10 and S12 are trans-substituted linking groups Q1 and Q2, or (iv) S9 and S11 are trans-substituted linking groups Q1 and Q2; and
Q1 and Q2 are independently selected linking groups of the formula:
wherein:
n is from 0 or 1 to 5 or 10;
R3 may be present or absent;
R1, R2, and R3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl; and
Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkylthiol, formyl, halo, alkenyl, alkynyl, haloalkyl, dialkyl phosphonate, alkyl sulfonate, acetylacetone, and dialkyl boronate groups.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein S9 and S11 are trans-substituted linking groups Q1 and Q2.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein S10 and S12 are trans-substituted lining groups Q1 and Q2.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein neither S8 nor S14 is H.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein M is Zn or Mg.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, and CH.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein K1, K2, K3, and K4 are all N.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein S4, S7, S8, S9, S10, S11, S12, and S14 are all alkyl.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein K1, K2, K3, and K4 are independently selected from the group consisting of N, O, S, and CH.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein K1, K2, K3, and K4 are all N.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein S4, S8, and S14 are all alkyl.

### Claim 12

A trans substituted oxochlorin compound of Formula X:
wherein:
M is absent;
K1, K2, K3, and K4 are independently selected from the group consisting of N, 0, 5, Se, Te, and CH;
S1, S2, S3S4, S5, S6, S8, S9, S10, S11, S12, and S14 are independently selected from the group consisting of H, aryl, alkyl, cycloalkyl, spiroalkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, periluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl;
wherein S7 and S13 are together ═O;
and wherein either (i) S10 and S12 are trans-substituted linking groups Q1 and Q2, or S9 and S11 are trans-substituted linking groups Q1 and Q2; and
Q1 and Q2 are independently selected linking groups of the formula:
wherein:
n is from 0 or 1 to 5 or 10;
R3 may be present or absent;
R1, R2, and R3 are each independently selected from the group consisting of ethene, ethyne, aryl, and heteroaryl groups, which aryl and heteroaryl groups may be unsubstituted or substituted one or more times with H, aryl, phenyl, cycloalkyl, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkylthio, perfluoroalkyl, perfluoroaryl, pyridyl, cyano, thiocyanato, nitro, amino, alkylamino, acyl, sulfoxyl, sulfonyl, imido, amido, and carbamoyl; and
Y is a protected or unprotected reactive substituent selected from the group consisting of hydroxy, thio, seleno, telluro, ester, carboxylic acid, boronic acid, phenol, silane, sulfonic acid, phosphonic acid, alkyithiol, formyl, halo, alkenyl, alkynyl, haloalkyl, dialkyl phosphonate, alkyl sulfonate, acetylacetone, and dialkyl boronate groups.

### Claim 13 (depends on 12)

The compound according to claim 12, wherein S9 and S11 are trans-substituted linking groups Q1 and Q2.

### Claim 14 (depends on 12)

The compound according to claim 12, wherein S10 and 12 are trans-substituted linking groups Q1 and Q2.

### Claim 15 (depends on 12)

The compound according to claim 12, wherein neither S8 nor S14 is H.