US 9,425,413 B2Granted

Conjugated side-strapped phthalocyanines and methods for producing and using the same

AssigneeArizona Board of Regents on Behalf of the University of Arizona

InventorsDominic V. McGrath, Neal R. Armstrong

Life of this patent

Estimating the term…

Abstract

The present invention provides conjugated side-strapped phthalocyanines and methods for producing and using the same. In one particular embodiment, the conjugated side-strapped phthalocyanine is of the formula: where each of the substituents are defined herein.

Claims13

Dependent claims

A conjugated side-strapped phthalocyanine compound of the formula:

wherein
M is a phthalocyanine coordinating moiety;
at least one pair of RW1 and RW2, or RN1 and RN2, or RE1 and RE2, or RS1 and RS2 form a conjugated side-strapped substituent and the remaining are independently selected from the group consisting of:
(i) H;
(ii) C1-C25 alkyl;
(iii) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(iv) an aryl or a heteroaryl group of the formula
wherein E is S, O, or NH, and RF1, RF2, RF3, RF4, RF5, RF6, RF7, and RF8 are independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) —NRe1Re2, —ORe3, and —SRe4;
(e) an aryl or heteroaryl group;
and
(f) a polymerizable group;
(v) a fused aromatic ring of the formula:
(vi) a polymerizable group selected from the group consisting of vinyl, allyl, 4-styryl, acryloyl, methacroyl, epoxide, acrylonitrile, isocyanate, isothiocyanate, strained ring olefins;
—(CH2)dSiCl3, —(CH2)dSi(OCH2CH3)3, and —(CH2)dSi(OCH3)3;
(vii) halide;
and
(viii) —NRe1Re2, —ORe3, or —SRe4;
each of RA1, RA2, RB1, RB2, RC1, RC2, RD1 and RD2 is independently selected from the group consisting of:
(i) H;
(ii) C1-C25 alkyl;
(iii) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, —(CH2CH2O)a—(CH2)b-ethynyl;
(iv) an aryl or heteroaryl group of the formula
wherein E is S, O, or NH, and RF1, RF2, RF3, RF4, RF5, RF6, RF7, and RF8 are independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) —NRe1Re2, —ORe3, and —SRe4;
(e) an aryl or heteroaryl group;
and
(f) a polymerizable group;
(v) a fused aromatic ring of the formula:
(vi) a polymerizable group selected from the group consisting of vinyl, allyl, 4-styryl, acryloyl, methacroyl, epoxide, acrylonitrile, isocyanate, isothiocyanate, strained ring olefins;
—(CH2)dSiCl3, —(CH2)dSi(OCH2CH3)3, and —(CH2)dSi(OCH3)3;
(vii) halide;
(viii) —NRe1Re2, —ORe3, or —SRe4;
or each pair of RA1 and RA2, RB1 and RB2, RC1 and RC2, and RD1 and RD2 along with the carbon atom to which they are attached to form an optionally substituted phenyl ring moiety;
a is an integer from 0 to 10;
b is an integer from 1 to 25;
d is an integer between 0 and 25;
each of Re1, Re2, Re3, and Re4 is independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) an aryl or heteroaryl group;
and
(e) a polymerizable group;
and
each of Ra1, Ra2, and Ra3 is independently selected from the group consisting of H, C1-C25 alkyl and aryl.

54 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/672,124Filed 28 Mar 2015 · us provisional application
Priority: 29 Mar 2014
Published: US 2015/0280143 A11 Oct 2015
Granted: 23 Aug 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 487/22
Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 -…:…
H10K 85/311
Coordination compounds: phthalocyanine
H10K 30/30
Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation: comprising bulk…
H10K 30/50
Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation: photovoltaic…

Family

Application61/972,230Us provisional application · filed 29 Mar 2014
US 2015/0280143 A1Pre-grant publication · published 1 Oct 2015
US 9,425,413 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A conjugated side-strapped phthalocyanine compound of the formula:

wherein
M is a phthalocyanine coordinating moiety;
at least one pair of RW1 and RW2, or RN1 and RN2, or RE1 and RE2, or RS1 and RS2 form a conjugated side-strapped substituent and the remaining are independently selected from the group consisting of:
(i) H;
(ii) C1-C25 alkyl;
(iii) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(iv) an aryl or a heteroaryl group of the formula
wherein E is S, O, or NH, and RF1, RF2, RF3, RF4, RF5, RF6, RF7, and RF8 are independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) —NRe1Re2, —ORe3, and —SRe4;
(e) an aryl or heteroaryl group;
and
(f) a polymerizable group;
(v) a fused aromatic ring of the formula:
(vi) a polymerizable group selected from the group consisting of vinyl, allyl, 4-styryl, acryloyl, methacroyl, epoxide, acrylonitrile, isocyanate, isothiocyanate, strained ring olefins;
—(CH2)dSiCl3, —(CH2)dSi(OCH2CH3)3, and —(CH2)dSi(OCH3)3;
(vii) halide;
and
(viii) —NRe1Re2, —ORe3, or —SRe4;
each of RA1, RA2, RB1, RB2, RC1, RC2, RD1 and RD2 is independently selected from the group consisting of:
(i) H;
(ii) C1-C25 alkyl;
(iii) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, —(CH2CH2O)a—(CH2)b-ethynyl;
(iv) an aryl or heteroaryl group of the formula
wherein E is S, O, or NH, and RF1, RF2, RF3, RF4, RF5, RF6, RF7, and RF8 are independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) —NRe1Re2, —ORe3, and —SRe4;
(e) an aryl or heteroaryl group;
and
(f) a polymerizable group;
(v) a fused aromatic ring of the formula:
(vi) a polymerizable group selected from the group consisting of vinyl, allyl, 4-styryl, acryloyl, methacroyl, epoxide, acrylonitrile, isocyanate, isothiocyanate, strained ring olefins;
—(CH2)dSiCl3, —(CH2)dSi(OCH2CH3)3, and —(CH2)dSi(OCH3)3;
(vii) halide;
(viii) —NRe1Re2, —ORe3, or —SRe4;
or each pair of RA1 and RA2, RB1 and RB2, RC1 and RC2, and RD1 and RD2 along with the carbon atom to which they are attached to form an optionally substituted phenyl ring moiety;
a is an integer from 0 to 10;
b is an integer from 1 to 25;
d is an integer between 0 and 25;
each of Re1, Re2, Re3, and Re4 is independently selected from the group consisting of:
(a) H;
(b) C1-C25 alkyl;
(c) a moiety of the formula:
—(CH2CH2O)a—(CH2)bORa1, —(CH2CH2O)a—(CH2)bNRa2Ra3, —(CH2CH2O)a—(CH2)bCONRa2Ra3, —(CH2CH2O)a—(CH2)bCN, —(CH2CH2O)a—(CH2)bCl, —(CH2CH2O)a—(CH2)bBr, —(CH2CH2O)a—(CH2)bI, —(CH2CH2O)a—(CH2)b-Phenyl, or —(CH2CH2O)a—(CH2)b-ethynyl;
(d) an aryl or heteroaryl group;
and
(e) a polymerizable group;
and
each of Ra1, Ra2, and Ra3 is independently selected from the group consisting of H, C1-C25 alkyl and aryl.

54 more elements

Facts

Application

14/672,124Filed 28 Mar 2015 · us provisional application

Priority

29 Mar 2014

Published

US 2015/0280143 A11 Oct 2015

Granted

23 Aug 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 487/22
Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 -…:…
H10K 85/311
Coordination compounds: phthalocyanine
H10K 30/30
Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation: comprising bulk…
H10K 30/50
Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation: photovoltaic…