Dye sensitized photoelectric conversion device

Patent metadata

Field	Value
Publication number	US-10170250-B2
Application number	US-201815918438-A
Country	US
Kind code	B2
Filing date	Mar 12, 2018
Priority date	May 20, 2015
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

An oxadiazole dye for use as an organic photosensitizer. The oxadiazole dye comprising donor-π-spacer-acceptor type molecules in which at least one of an oxadiazole group acts as a π-conjugated bridge (spacer), a naphthyl 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. The dye for use 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 photoelectric conversion device, comprising:
a layer, comprising:
an anode,
a semiconductor, and
a light absorbing compound;

an iodine redox couple electrolytic solution, and
a passive substrate, comprising:
a cathode,

wherein the semiconductor and the light absorbing compound are between the anode and the cathode,
wherein the light absorbing compound is chemisorbed on the semiconductor;
wherein the semiconductor is a metal oxide, 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 formula (II′), (III′), (IV′), or (V′):

A 3 is an aromatic hydrocarbon chromophore of formula (VI′), (VII′), or (VIII′)

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

2. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is selected from the group consisting of:
(E)-2-Cyano-3-(5-(5-(naphthalene-2-yl)-1,3,4-oxadiazol-2-yl)thiophen-2-yl)-acrylic acid;
(E)-2-Cyano-3-(5-(5-(naphthalene-2-yl)-1,2,3-oxadiazol-4-yl)thiophen-2-yl)-acrylic acid;
(E)-2-Cyano-3-(5-(5-(naphthalen-2-yl)-1,2,4-oxadiazol-3-yl)thiophen-2yl)-acrylic acid;
(E)-2-Cyano-3-(5-(4-(naphthalen-2-yl)-1,2,5-oxadiazol-3-yl)thiophen-2yl)-acrylic acid;
(E)-2-Cyano-3-(5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl)-acrylic acid;
(E)-2-Cyano-3-(5-(naphthalen-2-yl)-1,2,3-oxadiazol-4-yl)-acrylic acid;
(E)-2-Cyano-3-(5-(naphthalen-2-yl)-1,2,4-oxadiazol-3-yl)-acrylic acid;
(E)-2-Cyano-3-(4-(naphthalen-2-yl)-1,2,5-oxadiazol-3-yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl)thiophen-2-yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(5-(naphthalen-2-yl)-1,2,3-oxadiazol-4-yl)thiophen-2-yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(5-(naphthalen-2-yl)-1,2,4-oxadiazol-3-yl)thiophen-2yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(4-(naphthalen-2-yl)-1,2,5-oxadiazol-3-yl)thiophen-2yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(naphthalen-2-yl)-1,3,4-oxadiazol-2-yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(naphthalen-2-yl)-1,2,3-oxadiazol-4-yl)-acrylic acid;
(Z)-2-Cyano-3-(5-(naphthalen-2-yl)-1,2,4-oxadiazol-3-yl)-acrylic acid; and
(Z)-2-Cyano-3-(4-(naphthalen-2-yl)-1,2,5-oxadiazol-3-yl)-acrylic acid.

3. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (Ia)

4. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (Ib)

5. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IIa)

6. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IIb)

7. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IIIa)

8. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IIIb)

9. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IVa)

10. The dye sensitized photoelectric conversion device of claim 1 , wherein the light absorbing compound is represented by formula (IVb)

Assignees

• Univ King Fahd Pet & Minerals

Inventors

• Mehmood Umer
• Ahmed Shakeel
• Hussein Ibnelwaleed A

Classifications

• C09B23/105

  two >CH- groups · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title

• C07D271/08

  1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles · CPC title

• C07D271/06

  1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title