Double donor functionalisation of the peri-positions of perylene and naphthalene monoimide via versatile building blocks

Patent metadata

Field	Value
Publication number	US-9630973-B2
Application number	US-201314422254-A
Country	US
Kind code	B2
Filing date	Aug 27, 2013
Priority date	Aug 30, 2012
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

The present invention provides the compounds of formulae (3) and (1) wherein n is 0 or 1, R 13 and R 14 are the same or different and are selected from the group consisting of NHR 310 , NR 311 R 312 , OR 313 , SR 314 and R 315 , or R 13 and R 14 together are selected from the group consisting of (a), (b) and (c), and X is CI, Br of I, and a process for the preparation of compounds of formula (3) comprising the compounds of formula (1) as key intermediates.

First claim

The invention claimed is:

1. A compound of formula (3)

wherein
n is 0 or 1,
R 13 and R 14 are the same or different and are selected from the group consisting of NHR 310 , NR 311 R 312 , OR 313 , SR 314 and R 315 ,
wherein
R 310 , R 311 , R 312 , R 313 , R 314 and R 315 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl or heteroaryl, provided that R 315 does not represent a methyl group,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3010 R 3011 , O—R 3012 and S—R 3013 , and
C 6-14 -aryl and heteroaryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3014 R 3015 , O—R 3016 and S—R 3017 ,
wherein R 3010 , R 3011 , R 3012 , R 3013 , R 3014 , R 3015 , R 3016 and R 3017 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 13 and R 14 together are selected from the group consisting of

wherein
L 1 and L 2 are C 1-6 -alkylene, C 6-14 -arylene, or C 1-6 -alkylene-C 6-14 -arylene-C 1-6 -alkylene,
R 25 is H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl or heteroaryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3030 R 3031 , O—R 3032 and S—R 3033 , and
C 6-14 -aryl and heteroaryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3034 R 3035 , O—R 3036 and S—R 3037 ,
wherein R 3030 , R 3031 , R 3032 , R 3033 , R 3034 , R 3035 , R 3036 and R 3037 are the same or different and are C 1-10 -alkyl or phenyl,

L 3 is a direct bond, C 1-6 -alkylene, C 6-14 -arylene, or C 1-6 -alkylene-C 6-14 -arylene-C 1-6 -alkylene,
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R 300 , OR 301 , SR 302 , OC(O)R 303 , C(O)OR 304 and NR 305 R 306 ,
wherein R 300 , R 301 , R 302 , R 303 , R 304 , R 305 and R 306 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl or heteroaryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3000 R 3001 , O—R 3002 , S—R 3003 , NO 2 , CN and halogen, and
C 6-14 -aryl and heteroaryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3004 R 3005 , O—R 3006 , S—R 3007 , NO 2 , CN and halogen,
wherein R 3000 , R 3001 , R 3002 , R 3003 , R 3004 , R 3005 , R 3006 and R 3007 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 17 and R 19 , respectively, R 18 and R 20 together are

and
R 23 and R 24 together are

wherein
R 26 , R 27 and R 28 are H, C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl, C 6-14 -aryl or heteroaryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, COOM 1 , SO 3 M 1 , PO 3 M 1 , NO 2 , CN and halogen, and
C 6-14 -aryl and heteroaryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, COOM 1 , SO 3 M 1 , PO 3 M 1 , NO 2 , CN and halogen,
wherein M 1 is H, alkali metal or N(R 3020 R 3021 R 3022 R 3023 ),
 wherein R 3020 , R 3021 , R 3022 , and R 3023 are the same or different and are C 1-10 -alkyl,

or
R 27 and R 28 together with the unit

form a five or six membered ring which may be substituted with one or more substituents selected from the group consisting of COOM 2 , SO 3 M 2 , PO 3 M 2 , NO 2 , CN and halogen,
wherein M 2 is H, alkali metal or N(R 3024 R 3025 R 3026 R 3027 ),
wherein R 3024 , R 3025 , R 3026 , and R 3027 are the same or different and are C 1-10 -alkyl,

with the proviso that if n is 1, R 13 and R 14 are phenyl substituted with N(phenyl) 2 , R 15 , R 16 , R 17 , R 18 , R 21 and R 22 are H, one of R 19 and R 20 is phenyl substituted with N(phenyl) 2 , and the other of R 19 and R 20 is H or phenyl substituted with N(phenyl) 2 , then R 23 and R 24 together are not

wherein R 26 is 2-ethylhexyl.

2. The compound of claim 1 , wherein n is 1.

3. The compound of claim 2 , wherein R 15 , R 16 , R 21 and R 22 are H, and R 17 , R 18 , R 19 and R 20 are the same or different and are selected from the group consisting of H, F, Cl, Br, I, CN, R 300 , OR 301 , SR 302 , OC(O)R 303 , C(O)OR 304 and NR 305 R 306 ,
wherein R 300 , R 301 , R 302 , R 303 , R 304 , R 305 and R 306 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3000 R 3001 , O—R 3002 , S—R 3003 , NO 2 , CN and halogen, and
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3004 R 3005 , O—R 3006 , S—R 3007 , NO 2 , CN and halogen,
wherein R 3000 , R 3001 , R 3002 , R 3003 , R 3004 , R 3005 , R 3006 and R 3007 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 17 and R 19 , respectively, R 18 and R 20 together are

4. The compound of claim 3 , wherein R 15 , R 16 , R 21 and R 22 are H, and R 17 , R 18 , R 19 and R 20 are the same or different and are H or Cl.

5. The compound of claim 1 , wherein R 13 and R 14 are the same or different and are selected from the group consisting of NHR 310 , NR 311 R 312 and R 315 ,
wherein
R 310 , R 311 , R 312 and R 315 are C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl, C 5-8 -cycloalkyl or C 6-14 -aryl, provided that R 315 does not represent a methyl group,
wherein
C 1-20 -alkyl, C 2-20 -alkenyl, C 2-20 -alkynyl and C 5-8 -cycloalkyl may be substituted with one or more substituents selected from the group consisting of phenyl, NR 3010 R 3011 , O—R 3012 and S—R 3013 , and
C 6-14 -aryl may be substituted with one or more substituents selected from the group consisting of C 1-10 -alkyl, NR 3014 R 3015 , O—R 3016 and S—R 3017 ,
wherein R 3010 , R 3011 , R 3012 , R 3013 , R 3014 , R 3015 , R 3016 and R 3017 are the same or different and are C 1-10 -alkyl or phenyl,

or
R 13 and R 14 together are selected from the group consisting of

wherein
L 2 is C 1-6 -alkylene, C 6-14 -arylene, or C 1-6 -alkylene-C 6-14

Assignees

• Basf Se
• Max-Planck-Gesellschaft Zur Foerderung Der Wss E V
• Max-Planck-Gesellschaft Zur Förderung Der Wss E V

Inventors

• Wonneberger Henrike
• Reichelt Helmut
• Zagranyarski Yulian
• Li Chen
• Muellen Klaus
• Chen Long

Classifications

• H01G9/2031

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• C07D491/06 Primary

  Peri-condensed systems · CPC title

• C07D239/70

  condensed with carbocyclic rings or ring systems · CPC title

• Y02B10/10

  Photovoltaic [PV] · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title