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Substituted porphyrins, porphyrin-containing polymers, and synthetic methods therefor

Assignee: University of Pennsylvania

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Filing: 1992-08-14

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Granted: 1994-12-06

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Expires: 2012-08-14

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Abstract

Abstract Porphyrins substituted with, for example, vinyl and acetylene groups are provided, along with polymers containing the same. In preferred embodiments, the substituted porphyrins are prepared by coupling halogenated porphyrins with carbon-centered anionic groups via metal-mediated crosscoupling reactions under stoichiometric or catalytic conditions.

Inventors

👤 Michael J. Therien
👤 Stephen G. DiMagno

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-11-01 08:58

CPC Classifications

A; A61; A61K; A61K41/00; A61K41/0057; A61K41/0071; A61K31/00; A61K31/33; A61K31/555; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/545; A61K47/546; A61K51/00; A61K51/02; A61K51/04; A61K51/0474; A61K51/0485; A61P; A61P31/00; A61P31/04; B; B01; B01J; B01J31/00; B01J31/02; B01J31/0234; B01J31/0235; B01J31/0244; B01J31/16; B01J31/165; B01J31/1658; B01J31/18; B01J31/1805; B01J31/181; B01J31/1815; B01J31/24; B01J31/2404; B01J31/2409; C; C07; C07C; C07C29/00; C07C29/48; C07C29/50; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/333; C07D487/00; C07D487/22; C07D519/00; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/0825; C07F7/0832; C08; C08F; C08F30/00; C08F30/04; C08G; C08G73/00; C08G73/06; C08G73/0605; C08G73/0611; C08G79/00; C09; C09B; C09B47/00; C09B69/00; C09B69/10; C09B69/108; G; G01; G01N; G01N27/00; G01N27/02; G01N27/04; G01N27/12; G01N27/125; G01N27/126; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0664; G03G5/0696; B01J2231/00; B01J2231/40; B01J2231/42; B01J2531/00; B01J2531/02; B01J2531/0238; B01J2531/0241; B01J2531/025; B01J2531/10; B01J2531/16; B01J2531/20; B01J2531/22; B01J2531/23; B01J2531/26; B01J2531/27; B01J2531/40; B01J2531/42; B01J2531/48; B01J2531/80; B01J2531/82; B01J2531/824

Claims Analysis

Total Claims: 50

Claim 1

Independent Claim 278 words

A compound having formula (1) or (2): ##STR7## wherein: (a) at least two of R A1 -R A4 has formula CH═CH 2 ; or (b) at least one of R B1 -R B8 has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H; or (c) at least two of R B1 -R B8 have formula C═C(R D ); or (d) at least one of R A1 -R A4 is haloalkyl having 1 to about 20 carbon atoms; or (e) at least one of R B1 -R B8 is haloalkyl having 2 to about 20 carbon atoms; or (f) at least five of R B1 -R B8 are haloalkyl having 1 to about 20 carbon atoms or haloaryl having about 6 to about 20 carbon atoms; or (h) at least one of R A1 -R A4 has formula C(R C )═C(R D )(R E ), provided that at least two of R C , R D and R E are not H; or (i) at least two of R A1 -R A4 have formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H; where R C , R D , and R E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinatol; and M is a chelated metal atom.

Claim 2

Dependent Claim 278 words

Claim 3

Dependent Claim 19 words

The compound of claim 1 wherein at least two of R A1 -R A4 has formula CH═CH 2 .

Claim 4

Dependent Claim 41 words

The compound of claim 1 wherein at least one of R B1 -R B8 has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H.

Claim 5

Dependent Claim 19 words

The compound of claim 1 wherein at least two of R B1 -R B8 have formula C═C(R D ).

Claim 6

Dependent Claim 23 words

The compound of claim 1 wherein at least one of R A1 -R A4 is haloalkyl having 1 to about 20 carbon atoms.

Claim 7

Dependent Claim 23 words

The compound of claim 1 wherein at least one of R B1 -R B8 is haloalkyl having 2 to about 20 carbon atoms.

Claim 8

Dependent Claim 24 words

The compound of claim 1 wherein at least five of R B1 -R B8 are haloalkyl having from 1 to about 20 carbon atoms.

Claim 9

Dependent Claim 24 words

The compound of claim 1 wherein at least one of R B1 -R B8 is haloaryl having about 6 to about 20 carbon atoms.

Claim 10

Dependent Claim 24 words

The compound of claim 1 wherein at least one of R B1 -R B8 is haloaryl having about 6 to about 20 carbon atoms.

Claim 11

Dependent Claim 32 words

The compound of claim 1 wherein at least one of R B1 -R B8 is alkyl having 1 to about 20 carbon atoms or aryl having 6 to about 20 carbon atoms.

Claim 12

Dependent Claim 38 words

The compound of claim 10 wherein R B5 has formula C═C(R D ) and each of R A1 -R A4 are alkyl having 1 to about 20 carbon atoms or aryl having 6 to about 20 carbon atoms.

Claim 13

Dependent Claim 41 words

The compound of claim 10 wherein R B1 and R B5 have formula C═C(R D ) and each of R A1 -R A4 are alkyl having 1 to about 20 carbon atoms or aryl having 6 to about 20 carbon atoms.

Claim 14

Dependent Claim 41 words

The compound of claim 10 wherein R B2 and R B5 have formula C═C(R D ) and each of R A1 -R A4 are alkyl having 1 to about 20 carbon atoms or aryl having 6 to about 20 carbon atoms.

Claim 15

Dependent Claim 42 words

The compound of claim 10 wherein each of R B1 -R B8 have formula C═C(R D ) and each of R A1 -R A4 are alkyl having 1 to about 20 carbon atoms or aryl having 6 to about 20 carbon atoms.

Claim 16

Dependent Claim 37 words

The compound of claim 10 wherein at least one of R B1 -R B8 is H, alkyl having 1 to about 20 carbon atoms, aryl having 6 to about 20 carbon atoms, F, Cl, Br, or I.

Claim 17

Dependent Claim 89 words

The compound of claim 15 wherein R A1 has formula C═C(R D ), each of R A2 -R A4 are alkyl having 1 to about 20 carbon atoms, aryl having 6 to about 20 carbon atoms, F, Cl, Br, or I, and R D is H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato.

Claim 18

Dependent Claim 91 words

The compound of claim 15 wherein R A1 and R A3 have formula C═C(R D ), R A2 and R A4 are alkyl having 1 to about 20 carbon atoms, aryl having 6 to about 20 carbon atoms, F, Cl, Br, or I, and R D is H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, triaikylsilyl, or porphyrinato.

Claim 19

Dependent Claim 28 words

The compound of claim 17 wherein R D is 3,4,5-trialkyl-substituted phenyl or 3,4,5-trialkyloxy-substituted phenyl wherein said alkyl and alkoxy substituents have about 7 to about 20 carbon atoms.

Claim 20

Dependent Claim 63 words

The compound of claim 15 wherein R A1 -R A4 have formula C═C(R D ) and R D is H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato.

Claim 21

Dependent Claim 28 words

The compound of claim 19 wherein R D is 3,4,5-trialkyl-substituted phenyl or 3,4,5-trialkyloxy-substituted phenyl wherein said alkyl and alkoxy substituents have about 7 to about 20 carbon atoms.

Claim 22

Dependent Claim 43 words

The compound of claim 1 wherein M is a lanthanide or actinide or Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Y, Zr, Nb, Mo, Ru, Rh, Pd, Ag, La, Hf, Ta, W, Re, Os, Ir, Pt, Cd, Hg, Li or Au.

Claim 23

Dependent Claim 15 words

The compound of claim 1 wherein M is a metal having a full valence shell.

Claim 24

Dependent Claim 11 words

The compound of claim 1 wherein M is Zn or Mg.

Claim 25

Dependent Claim 134 words

A compound having formula (1) or (2): ##STR8## wherein: at least one of R A1 -R A4 or R B1 -R B8 is a halogen; and at least one of the remaining R A1 -R A4 or R B1 -R B8 is C(R C )═C(R D )(R E ), C═C(R D ), haloalkyl having from 1 to about 20 carbon atoms, or haloaryl having about 6 to about 20 carbon atoms where R C , R D , and R E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato; and M is a chelated metal atom.

Claim 26

Dependent Claim 134 words

Claim 27

Dependent Claim 50 words

A compound having formula (1) or (2): ##STR9## wherein M is a chelated metal atom and at least one of R A1 -R A4 or R B1 -R B8 has formula Y(L) 2 X A where Y is a metal, L is a ligand, and X A is a halogen.

Claim 28

Dependent Claim 50 words

Claim 29

Dependent Claim 74 words

A compound having formula (1) or (2): ##STR10## wherein at least one of R A1 -R A4 or R B1 -R B8 has formula Y(L) 2 R O where M is a chelated metal atom, Y is a metal; L is a ligand; and R O is alkyl having 1 to about 10 carbon atoms, alkenyl or alkynyl having 2 to about 10 carbon atoms, aryl having bout 6 to about 20 carbon atoms.

Claim 30

Dependent Claim 74 words

Claim 31

Dependent Claim 17 words

The compound of claim 1 wherein at least one of R A2 and R A4 are halogen.

Claim 32

Dependent Claim 186 words

A compound having formula (1) or (2): ##STR11## wherein: (a) R A1 has formula C═C(R D ) provided that R D is not H or alkyl having 1 to about 20 carbon atoms; or (b) R A1 and R A2 have formula C═C(R D ); or (c) R A1 and R A3 have formula C═C(R D ) and R A2 and R A4 are not H; or (d) R A1 , R A2 , and R A3 have formula C═C(R D ); or (e) R A1 -R A4 have formula C═C(R D ) provided that R B1 -R B8 are not H or alkyl having 1 to about 20 carbon atoms; or (f) R A1 -R A4 have formula C═C(R D ) provided that R D is not H or trialkylsilyl; where R D is H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato; and M is a chelated metal atom.

Claim 33

Dependent Claim 186 words

Claim 34

Dependent Claim 29 words

The compound of claim 28 wherein R A1 has formula C═C(R D ) provided that R D is not H or alkyl having 1 to about 20 carbon atoms.

Claim 35

Dependent Claim 16 words

The compound of claim 28 wherein R A1 and R A2 have formula C═C(R D ).

Claim 36

Dependent Claim 25 words

The compound of claim 28 wherein R A1 and R A3 have formula C═C(R D ) and R A2 and R A4 are not H.

Claim 37

Dependent Claim 20 words

The compound of claim 28 wherein R A1 , R A2 , and R A3 have formula C═C(R D ).

Claim 38

Dependent Claim 33 words

The compound of claim 28 wherein R A1 -R A4 have formula C═C(R D ) provided that R B1 -R B8 are not H or alkyl having 1 to about 20 carbon atoms.

Claim 39

Dependent Claim 24 words

The compound of claim 28 wherein R A1 -R A4 have formula C═C(R D ) provided that R D is not H or trimethylsilyl.

Claim 40

Dependent Claim 263 words

A compound having formula (1) or (2): ##STR12## wherein: (a) R A1 has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H; or (b) R A1 and R A2 have formula C(R C )═C(R D )(R E ); or (c) R A1 and R A3 have formula C(R C )═C(R D )(R E ); or (d) R A1 , R A2 , and R A3 have formula C(R C )═C(R D )(R E ); or (e) R A1 -R A4 have has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H and that R D and R E are not H, alkyl having from 1 to about 20 carbon atoms; or aryl having about 6 to about 20 carbon atoms; or (f) R A1 -R A4 have formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H and that at east two of R B1 -R B8 are not H; where R C , R D , and R E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato; and M is a chelated metal atom.

Claim 41

Dependent Claim 263 words

Claim 42

Dependent Claim 35 words

The compound of claim 35 wherein R A1 has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H.

Claim 43

Dependent Claim 20 words

The compound of claim 35 wherein R A1 and R A2 have formula C(R C )═C(R D )(R E ).

Claim 44

Dependent Claim 20 words

The compound of claim 35 wherein R A1 and R A3 have formula C(R C )═C(R D )(R E ).

Claim 45

Dependent Claim 24 words

The compound of claim 35 wherein R A1 , R A2 , and R A3 have formula C(R C )═C(R D )(R E ).

Claim 46

Dependent Claim 66 words

The compound of claim 35 wherein R A1 -R A4 have has formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H and that R D and R E are not H, alkyl having from 1 to about 20 carbon atoms; or aryl having about 6 to about 20 carbon

Claim 47

Dependent Claim 50 words

The compound of claim 35 wherein R A1 -R A4 have formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H and that at least two of R B1 -R B8 are not H.

Claim 48

Dependent Claim 94 words

The compound of claim 26 wherein R O is C(R C )═C(R D )(R E ), C═C(R D ), haloalkyl having from 1 to about 20 carbon atoms, or haloaryl having about 6 to about 20 carbon atoms, and R C , R D , and R E are, independently, H, F, Cl, Br, I, alkyl having from 1 to about 20 carbon atoms, aryl having about 6 to about 20 carbon atoms, alkenyl having from 1 to about 20 carbon atoms, alkynyl having from 1 to about 20 carbon atoms, trialkylsilyl, or porphyrinato.

Claim 49

Dependent Claim 40 words

The compound of claim 1 wherein at least one of R A1 -R A4 has formula C(R C )═C(R D )(R E ), provided that at least two of R C , R D and R E are not H.

Claim 50

Dependent Claim 41 words

The compound of claim 1 wherein at least two of R A1 -R A4 have formula C(R C )═C(R D )(R E ), provided that at least one of R C , R D , and R E is not H.

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USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1997-12-05	1998-06-06	1998-12-06	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2001-12-05	2002-06-06	2002-12-06	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2005-12-05	2006-06-06	2006-12-06	$7700.00	Window Closed / Lapsed

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