Derivatives of pyrrolopyrrole cyanines and uses thereof

Patent metadata

Field	Value
Publication number	US-12410198-B2
Application number	US-202118259567-A
Country	US
Kind code	B2
Filing date	Dec 21, 2021
Priority date	Dec 28, 2020
Publication date	Sep 9, 2025
Grant date	Sep 9, 2025

Abstract

Disclosed is a compound having the following formula (1):as well as to the use of such as a dye sensitizer.Also disclosed is a dye sensitized solar cell including at least one compound of formula (I) as dye sensitizer.

First claim

The invention claimed is:

1. A compound having the following formula (I):

wherein:
Ar is selected from the group consisting of:
a phenyl group; and
a phenyl group substituted with at least one substituent L selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

Y is selected from the group consisting of:
a phenylene radical; and
a thiophenylene radical;
a furanylene radical; and

W is a phenyl group comprising at least one substituent Z,
wherein Z is selected from the group consisting of:
(C 1 -C 12 )alkyl groups;
(C 1 -C 12 )alkoxy groups; and
di((C 1 -C 12 )alkyl)amino groups;

R 1 is H;
R 2 is an anchoring group selected from the group consisting of:
a —COOH group;
a —C(═O)—NH(OH) group;
a —CH═C(CN)(COOH) group; and
a —PO 3 H 2 group;

R 3 is selected from the group consisting of:
H;
an anchoring group selected from the group consisting of:
a —COOH group;
a —C(═O)—NH(OH) group;
a —CH═C(CN)(COOH) group; and
a —PO 3 H 2 group;

(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups;
(C 1 -C 16 )thioalkyl groups; and
a group having the following formula (III):

wherein R 5 and R 6 , identical or different, are selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
a group having the following formula (IV):

R 7 being a (C 1 -C 16 )alkyl group;
a group having the following formula (V):

R a being a (C 1 -C 16 )alkyl group;
a group having the following formula (VI):

R 9 being a (C 1 -C 16 )alkyl group;
a group having the following formula (III-1):

wherein R′ 5 and R′ 6 , identical or different, are a group having the following formula (VI-1):

R′ 9 being a (C 1 -C 16 )alkyl group;

R 4 is selected from the group consisting of:
H;
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups;
(C 1 -C 16 )thioalkyl groups; and
a group having the following formula (VII):

wherein R 10 and R 11 , identical or different, are selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
a group having the following formula (VIII):

R 12 being a (C 1 -C 16 )alkyl group;
a group having the following formula (IX):

R 13 being a (C 1 -C 16 )alkyl group;
a group having the following formula (X):

R 14 being a (C 1 -C 16 )alkyl group.

2. The compound having the formula (I) of claim 1 , wherein Ar is selected from the group consisting of:
a phenyl group;
a substituted phenyl group comprising one substituent in ortho, meta or para position, having the following formula (1):

L being as defined in claim 1 ;

a substituted phenyl group having the following formula (2):

wherein
L 1 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

L 2 is H and L 3 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

or L 3 is H and L 2 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

a substituted phenyl group having the following formula (3):

wherein
L 4 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

L 5 is H and L 6 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

or L 6 is H and L 5 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups.

3. The compound having the formula (I) of claim 1 , wherein Ar is selected from the group consisting of:
a phenyl group;
a substituted phenyl group comprising one substituent in ortho, meta or para position, having the following formula (1):

L being as defined in claim 1 ;

a substituted phenyl group having the following formula (2):

wherein
L 1 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups;

L 2 is H and L 3 is identical to L 1 or L 3 is H and L 2 is identical to L 1 ; and

a substituted phenyl group having the following formula (3):

wherein
L 4 is selected from the group consisting of:
(C 1 -C 16 )alkyl groups;
(C 1 -C 16 )alkoxy groups; and
(C 1 -C 16 )thioalkyl groups; and

L 5 is H and L 6 is identical to L 4 or L 6 is H and L 5 is identical to L 4 .

4. The compound having the formula (I) of claim 1 , wherein Ar is a phenyl group, a p-tert-butylphenyl group or a phenyl group substituted with an alkoxy group.

5. The compound according to claim 1 , having the following formula (II):

wherein Ar, R 1 , R 2 , R 3 , R 4 , and W are as defined in claim 1 .

6. The compound according to claim 1 , wherein W is a group having one of the below formulae (4) to (7):

Z being as defined in claim 1 .

7. The compound according to claim 1 , wherein R 2 is a —COOH group.

8. The compound according to c

Assignees

• Centre Nat Rech Scient
• Univ Nantes
• Univ Picardie

Inventors

• Odobel Fabrice
• Pellegrin Yann
• Baron Thibaut
• Jacquemin Denis
• Sauvage Fréderic
• Naim Waad

Classifications

• Y02E10/542

  Dye sensitized solar cells · CPC title

• H01B1/121

  Charge-transfer complexes · CPC title

• H10K85/322

  comprising boron · CPC title

• H01G9/2063

  comprising a mixture of two or more dyes · CPC title

• H01G9/2059

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title