Oxadiazole based photosensitizers for use in dye-sensitive solar cells and photodynamic therapy

Patent metadata

Field	Value
Publication number	US-9892864-B2
Application number	US-201514720287-A
Country	US
Kind code	B2
Filing date	May 22, 2015
Priority date	May 22, 2015
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

An oxadiazole dye for use as an organic photosensitizer. The oxadiazole dye comprising donor-π-spacer-acceptor type portions in which at least one of an oxadiazole isomer acts as a π-conjugated bridge (spacer), a biphenyl unit acts as an electron-donating unit, a carboxyl group act as an electron acceptor group, and a cyano group acts as an anchor group. An optional thiophene group acts as part of the π-conjugated bridge (spacer). The dye for use as organic photosensitizers in a dye-sensitized solar cell and in photodynamic therapies. Computational DFT and time dependent DFT (TD-DFT) modeling techniques showing Light Harvesting Efficiency (LHE), Free Energy for Electron Injection (ΔG inject ), Excitation Energies, and Frontier Molecular Orbitals (FMOs) indicate that the series of dye comprise a more negative ΔG inject and a higher LHE value; resulting in a higher incident photon to current efficiency (IPCE).

First claim

The invention claimed is:

1. A dye sensitized solar cell, comprising:
an anode,
a cathode,
an electrolyte between the anode and the cathode,
a light absorbing layer comprising a semiconductor and a light absorbing compound,
wherein the light-absorbing compound is chemisorbed on the semiconductor; and
wherein the light absorbing compound has formula (I):

wherein A 1 is a divalent thiophene group of formula (I′)

A 2 is a divalent 5-membered heterocyclic group of at least one of formula (II′), (III′), (IV′), and (V′):

A 3 is an aromatic hydrocarbon chromophore of formula (VI′)

wherein R 1 is H, OH, C1-C6 alkyl, Cl, Br, F, or I, p is from 1-3, m is from 1-5, and n is from 0-5.

2. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound of the formula (I) is an (E) isomer.

3. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound of the formula (I) is a (Z) isomer.

4. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is at least one selected from the group consisting of
(E)-3-(5-([1,1′-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)-2-cyanoacrylic acid;
(E)-3-(5-([1,1′-biphenyl]-4-yl)-1,2,3-oxadiazol-4-yl)-2-cyanoacrylic acid;
(E)-3-(5-([1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)-2-cyanoacrylic acid;
(E)-3-(4-([1,1′-biphenyl]-4-yl)-1,2,5-oxadiazol-3-yl)-2-cyanoacrylic acid;
(E)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)thiophen-2-yl)-2-cyanoacrylic acid;
(E)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,2,3-oxadiazol-4-yl)thiophen-2-yl)-2-cyanoacrylic acid;
(E)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)thiophen-2-yl)-2-cyanoacrylic acid;
(E)-3-(5-(4-([1,1′-biphenyl]-4-yl)-1,2,5-oxadiazol-3-yl)thiophen-2-yl)-2-cyanoacrylic acid; and
(Z)-3-(5-([1,1′-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)-2-cyanoacrylic acid;
(Z)-3-(5-([1,1′-biphenyl]-4-yl)-1,2,3-oxadiazol-4-yl)-2-cyanoacrylic acid;
(Z)-3-(5-([1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)-2-cyanoacrylic acid;
(Z)-3-(4-([1,1′-biphenyl]-4-yl)-1,2,5-oxadiazol-3-yl)-2-cyanoacrylic acid;
(Z)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)thiophen-2-yl)-2-cyanoacrylic acid;
(Z)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,2,3-oxadiazol-4-yl)thiophen-2-yl)-2-cyanoacrylic acid;
(Z)-3-(5-(5-([1,1′-biphenyl]-4-yl)-1,2,4-oxadiazol-3-yl)thiophen-2-yl)-2-cyanoacrylic acid; and
(Z)-3-(5-(4-([1,1′-biphenyl]-4-yl)-1,2,5-oxadiazol-3-yl)thiophen-2-yl)-2-cyanoacrylic acid.

5. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (Ia)

6. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (Ib)

7. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IIa)

8. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IIb)

9. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IIIa)

10. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IIIb)

11. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IVa)

12. The dye sensitized solar cell of claim 1 , wherein the light absorbing compound is represented by formula (IVb)

Assignees

• Univ King Fahd Pet & Minerals

Inventors

• Mehmood Umer
• Ahmed Shakeel
• A Hussein Ibnelwaleed

Classifications

• H01G9/2059 Primary

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

• H01G9/2027

  comprising an oxide semiconductor electrode · CPC title

• H01L51/007

  Electricity · mapped topic

• H01L51/0068

  Electricity · mapped topic

• H01G9/2018

  characterised by the ionic charge transport species, e.g. redox shuttles · CPC title