Emissive sensors and devices incorporating these sensors

• US 20050147534A1
• Filed: 04/12/2004
• Published: 07/07/2005
• Est. Priority Date: 05/05/1998
• Status: Abandoned Application

• Current Assignee: Massachusetts Institute of Technology
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Kim, Tae-Hyun, Swager, Timothy M., Zhang, Shi-Wei
• Application Number:
  US10/823,093
• Publication Number:
  US 20050147534A1
• Time in Patent Office: Days
• US Class Current: 422/82.50
• 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, but are not limited to, electrophiles, alkylating agents, thionyl halides, and phosphate ester groups including phophoryl 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.

Claims

1-31. -31. (canceled)

32. A composition, comprising:

a compound having a structure;

comprising an organic moiety, {umlaut over (Q)} being one of nitrogen or oxygen, and Y being one of H or SiR₃, each R independently being one of hydrogen and an organic moiety,

wherein at least a portion of the compound is able to cyclize upon reaction of the compound with an electrophile able to transform OY into an alkylating agent.

33. The composition of claim 32, wherein the electrophile comprises a phosphate ester.

34. The composition of claim 32, wherein the electrophile comprises an electrophilic phosphorous, sulfur, or arsenic atom.

35. The composition of claim 34, wherein the electrophilic phosphorous, sulfur, or arsenic atom is bonded to more than one electron-withdrawing moiety.

36. The composition of claim 32, wherein the electrophile comprises an electrophilic carbon that is multiply-bonded another electrophilic atom.

37. The composition of claim 32, wherein the electrophile is a chemical warfare agent.

38. The composition of claim 32, wherein {umlaut over (Q)} is nitrogen.

39. The composition of claim 32, wherein {umlaut over (Q)} is oxygen.

40. The composition of claim 32, wherein the compound is a polymer.

41. The composition of claim 32, wherein a shortest bond path between O and {umlaut over (Q)} has at least 5 atoms.

42. The composition of claim 41, wherein a shortest bond path between O and {umlaut over (Q)} has exactly 5 atoms.

43. The composition of claim 32, wherein the compound is able to cyclize upon reaction of the compound with the electrophile to produce a product having a structure:

44. The composition of claim 32, wherein

45. The composition of claim 32, wherein

46. The composition of claim 45, wherein

47. The composition of claim 45, wherein

48. The composition of claim 45, wherein the structure

49. The composition of claim 48, wherein the two conjugated groups are not conjugated with each other.

50. The composition of claim 48, wherein the two conjugated groups are phenolic groups.

51. The composition of claim 48, wherein the structure

52. The composition of claim 45, wherein the compound comprises a structure:

53. The composition of claim 45, wherein the compound comprises a structure:

54. The composition of claim 45, wherein the compound comprises a structure:

55. The composition of claim 32, wherein the compound has a structure:

56. The composition of claim 55, wherein each of A⁵, A⁶, A⁷, and A⁸ independently is hydrogen.

57. The composition of claim 55, wherein the compound has a structure:

58. The composition of claim 57, wherein each of A⁵ and A⁶ independently is hydrogen.

59. The composition of claim 57, wherein A³ and A⁴ together comprise a conjugated group.

60. The composition of claim 59, wherein the conjugated group is cyclic.

61. The composition of claim 60, wherein the conjugated group is aromatic.

62. The composition of claim 55, wherein A¹ and A² together comprise a conjugated group.

63. The composition of claim 62, wherein the conjugated group is cyclic.

64. The composition of claim 55, wherein the compound has a structure:

65. The composition of claim 64, wherein at least one of A¹¹, A¹², A¹³, and A¹⁴ comprises a conjugated group.

81. The composition of claim 55, wherein the compound has a structure:

66-80. -80. (canceled)

82-126. -126. (canceled)

127. 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.

128. A method, comprising:

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

comprising an organic moiety, {umlaut over (Q)} being one of nitrogen or oxygen, and Y being one of H, an alkyl group, an alkoxy group, and SiR₃, each R independently being one of hydrogen and an organic moiety.

129-135. -135. (canceled)