Tunable photoactive compounds

Patent metadata

Field	Value
Publication number	US-9466798-B2
Application number	US-201313869325-A
Country	US
Kind code	B2
Filing date	Apr 24, 2013
Priority date	Mar 15, 2013
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

Photoactive compositions of matter, methods for their design and synthesis, and various applications of such compositions of matter are disclosed. Such photoactive compositions may, for example, include any one or more of the following: a core moiety; a primary electron donor moiety; an electron-withdrawing moiety; and an alkyl tail. Some photoactive compositions may further include multiple additional electron donor moieties, electron-withdrawing moieties, and alkyl tails. Methods for designing such photoactive compositions may include selecting a core moiety; selecting an electron-withdrawing moiety to add to the core moiety in order to modify the composition's electronic properties; selecting a primary electron donor moiety to be added in order to further modify the composition's electronic properties; selecting a second electron donor moiety to be added in order to modify the composition's electronic properties even further, if necessary; and synthesizing the designed composition.

First claim

What is claimed is:

1. A method comprising:
synthesizing a photoactive compound comprising (E)-2-cyano-3[5-[9,9-diethyl-7-(4-methoxy-N-(-4-methoxyphenyl)anilino)fluoren-2-yl]thiazol-2-yl]prop-2-enoic acid by:
halogenating a fluorene moiety so as to form a 4,4′-dihalo fluorene;
alkylating the fluorene moiety so as to form a photoactive moiety comprising 9,9-diethyl, 4,4′-dihalo fluorene;
reacting, by a coupling reaction, the photoactive moiety with a first reactant comprising 4-methoxy-N-(-4-methoxyphenyl)aniline so as to form an electron-donor modified photoactive moiety that comprises 9,9-diethyl-2-halo-7(4-methoxy-N-(-4-methoxyphenyl)anilino)fluorene;
reacting, by a second coupling reaction, the photoactive moiety with a second reactant comprising thiazol so as to form an electron-donor modified photoactive moiety that comprises 9,9-diethyl-7-(4-methoxy-N-(-4-methoxyphenyl)anilino)fluoren-2-yl]thiazol;
reacting, by a group addition reaction, the electron-donor modified photoactive moiety with a third reactant comprising cyanoacetic acid so as to form (E)-2-cyano-3[5-[9,9-diethyl-7-(4-methoxy-N-(-4-methoxyphenyl)anilino)fluoren-2-yl]thiazol-2-yl]prop-2-enoic acid.

2. The method of claim 1 further comprising testing the photoactive compound for use in one or more applications selected from the group consisting of: heterojunction photovoltaic cells, hybrid photovoltaic cells, dye-sensitized solar cells, batteries, field-effect transistors, and light-emitting diodes.

3. The method of claim 2 further comprising optimizing the photoactive compound based at least in part upon testing of the photoactive compound, wherein optimizing the photoactive compound comprises any one or more of radiation, thermal treatments, chemical treatments, interfacial modification, and substituting one or more alkyl tails in place of a hydrogen atom of the photoactive compound.

4. The method of claim 3 further comprising synthesizing a modified photoactive compound that comprises the core moiety, the electron-withdrawing moiety, the primary electron donor moiety, the second electron donor moiety, and at least one of the one or more alkyl tails.

5. The method of claim 1 further comprising obtaining the photoactive core moiety from asphaltene.

6. The method of claim 5 wherein obtaining the photoactive core moiety comprises isolating the photoactive core moiety from asphaltene.

7. The method of claim 1 wherein each of selecting primary electron donor moiety and selecting a primary electron donor moiety is carried out on a computer-readable medium.

Assignees

• Irwin Michael D
• Chute Jerred A
• Maher Iii Robert D
• Hunt Energy Entpr Llc

Inventors

• Irwin Michael D
• Chute Jerred A
• Maher Iii Robert D

Classifications

• H01L51/0058 Primary

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• Y02E10/542

  Dye sensitized solar cells · CPC title

• Y02E10/549

  Organic PV cells · CPC title