EMISSIVE SENSORS AND DEVICES INCORPORATING THESE SENSORS

• US 20110142717A1
• Filed: 11/15/2010
• Published: 06/16/2011
• Est. Priority Date: 05/05/1998
• Status: Active Grant

• Current Assignee: Massachusetts Institute of Technology
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Kim, Tae-Hyun, Zhang, Shi-Wei, Swager, Timothy M.
• Granted Patent: US 8,367,001 B2
• Time in Patent Office: Days
• US Class Current: 422/82.08
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1408 Carbocyclic compounds
• CPC Class Codes: C09K 2211/1425 Non-condensed systems
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/701 Organic molecular electronic devices
• CPC Class Codes: H10K 30/65 Light-sensitive field-effect devices, e.g. phototransistors
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/154 Ladder-type polymers
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/649 Aromatic compounds comprising a hetero atom
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: Y02E 10/549 Organic PV cells
• CPC Class Codes: Y10T 436/163333 Organic [e.g., chemical warfare agents, insecticides, etc.]
• CPC Class Codes: Y10T 436/17 Nitrogen containing
• CPC Class Codes: Y10T 436/20 Oxygen containing

Abstract

The present invention generally relates to luminescent and/or optically absorbing compositions and/or precursors to those compositions, including solid films incorporating these compositions/precursors, exhibiting increased luminescent lifetimes, quantum yields, enhanced stabilities and/or amplified emissions. The present invention also relates to sensors and methods for sensing analytes through luminescent and/or optically absorbing properties of these compositions and/or precursors. Examples of analytes detectable by the invention include electrophiles, alkylating agents, thionyl halides, and phosphate ester groups including phosphoryl halides, cyanides and thioates such as those found in certain chemical warfare agents. The present invention additionally relates to devices and methods for amplifying emissions, such as those produced using the above-described compositions and/or precursors, by incorporating the composition and/or precursor within a polymer having an energy migration pathway. In some cases, the compositions and/or precursors thereof include a compound capable of undergoing a cyclization reaction.

Claims

1-135. -135. (canceled)

136. A sensor, comprising:

a compound having a structure;

137. The sensor of claim 136, wherein the electrophile-comprises a phosphate ester.

138. The sensor of claim 136, wherein the electrophile comprises an electrophilic phosphorous, sulfur, or arsenic atom.

139. The sensor of claim 138, wherein the electrophilic phosphorous, sulfur, or arsenic atom is bonded to more than one electron-withdrawing moiety.

140. The sensor of claim 136, wherein the electrophile comprises an electrophilic carbon that is multiply-bonded another electrophilic atom.

141. The sensor of claim 136, wherein the electrophile is a chemical warfare agent.

142. The sensor of claim 136, wherein {umlaut over (Q)} is nitrogen.

143. The sensor of claim 136, wherein {umlaut over (Q)} is oxygen.

144. The sensor of claim 136, wherein the compound is a polymer.

145. The sensor of claim 136, wherein a shortest bond path between O and {umlaut over (Q)} has at least 5 atoms.

146. The sensor of claim 145, wherein a shortest bond path between O and {umlaut over (Q)} has exactly 5 atoms.

147. The sensor of claim 136, wherein the compound is able to cyclize upon reaction of the compound with the electrophile to produce a product having a structure:

148. The sensor of claim 136, wherein

149. The sensor of claim 136, wherein

150. The sensor of claim 149, wherein

151. The sensor of claim 149, wherein

152. The sensor of claim 149, wherein the structure

153. The sensor of claim 152, wherein the two conjugated groups are not conjugated with each other.

154. The sensor of claim 152, wherein the two conjugated groups are phenolic groups.

155. The sensor of claim 152, wherein the structure

156. The sensor of claim 149, wherein the compound comprises a structure:

157. The sensor of claim 149, wherein the compound comprises a structure:

158. The sensor of claim 149, wherein the compound comprises a structure:

159. The sensor of claim 136, wherein the compound has a structure:

160. The sensor of claim 159, wherein each of A⁵, A⁶, A⁷, and A⁸ independently is hydrogen.

161. The sensor of claim 159, wherein the compound has a structure:

162. The sensor of claim 161, wherein each of A⁵ and A⁶ independently is hydrogen.

163. The sensor of claim 161, wherein A³ and A⁴ together comprise a conjugated group.

164. The sensor of claim 163, wherein the conjugated group is cyclic.

165. The sensor of claim 164, wherein the conjugated group is aromatic.

166. The sensor of claim 159, wherein A¹ and A² together comprise a conjugated group.

167. The sensor of claim 166, wherein the conjugated group is cyclic.

168. The sensor of claim 159, wherein the compound has a structure:

169. The sensor of claim 168, wherein at least one of A¹¹, A¹², A¹³, and A¹⁴ comprises a conjugated group.

170. The sensor of claim 159, wherein the compound has a structure:

171. The sensor of claim 136, wherein the intramolecular cyclization reaction comprises an intramolecular nucleophilic substitution reaction.

172. The sensor of claim 136, wherein the cyclized product has a greater emissivity than the compound.

173. The sensor of claim 136, wherein the compound has the following structure,

174. The sensor of claim 136, wherein the electrophile is sarin, phosgene, soman, tabun, thionyl chloride,

175. A method, comprising:

reacting a compound with an electrophile to produce a product having greater emissivity than the compound, wherein the product comprises at least a portion of the compound that has been cyclized upon reaction with the electrophile.

176. A method, comprising:

cyclizing at least a portion of a compound by reacting the compound with an electrophile, the compound having a structure;