Conjugated Side-Strapped Phthalocyanines and Methods For Producing and Using The Same

摘要

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.

主权项

1. 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, Rc, 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; andeach of Ra1, Ra2, and Ra3 is independently selected from the group consisting of H, C1-C25 alkyl and aryl.