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EP-3320329-B1 - SENSOR COMPOUNDS AND ASSOCIATED METHODS AND DEVICES

EP3320329B1EP 3320329 B1EP3320329 B1EP 3320329B1EP-3320329-B1

Inventors

  • ZANG, LING
  • SLATTUM, PAUL

Dates

Publication Date
20260513
Application Date
20160711

Claims (9)

  1. A method of detecting a non-explosive analyte, comprising: exposing a sensor compound to a non-explosive analyte, wherein the sensor compound is a nanofiber structure; and displaying a change in photocurrent of the sensor compound upon exposure of the sensor compound to the non-explosive analyte, wherein the sensor compound is a compound having a structure according to Formula II: where R1 is chosen from C 1 -C 20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, where R2 is: a group having a nitrogen-containing side group selected from the group consisting of and and where R3-R10 are independently chosen from hydrogen, halides, carboxyl groups, nitrile groups, and C 1 -C 8 alkyl groups.
  2. The method of claim 1, wherein either: a. R1 is a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group; b. R1 is a C 4 -C 16 substituted or unsubstituted linear aliphatic group; c. R1 is a C 4 -C 16 substituted or unsubstituted branched aliphatic group; d. R1 is a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group, wherein at least one hydrogen of R1 has been substituted with a halide; or e. R1 is a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group, wherein at least one hydrogen of R1 has been substituted with a halide, wherein the halide is fluorine.
  3. The method of claim 1, wherein either: a. R1 comprises an ether group, a heterocycle group, an amine group, or an amide group; b. at least one of R3-R10 is not hydrogen; or c. at least two of R3-R10 are a halide, a carboxyl group, a nitrile group, or a C 1 -C 8 alkyl group.
  4. The method of claim 1, wherein the non-explosive analyte is selected from the group consisting of amine containing compounds, toxic industrial compounds, volatile organic compounds, chemical warfare agents, food safety compounds, and combinations thereof.
  5. A sensor compound detecting a target analyte, comprising: a sensor compound having a structure according to Formula II and formed as nanofiber structures: where R1 is chosen from C 2 -C 20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, and aryl groups, where R2 is: a group having a nitrogen-containing side group selected from the group consisting of and and where R3-R10 are independently chosen from hydrogen, halides, nitrile groups, and C 1 -C 8 alkyl groups.
  6. The sensor compound of claim 5, wherein R1 is either: a. a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group; b. a C 4 -C 16 substituted or unsubstituted linear aliphatic group; c. a C 4 -C 16 substituted or unsubstituted branched aliphatic group; d. a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group, wherein at least one hydrogen of R1 has been substituted with a halide; or e. a C 4 -C 16 substituted or unsubstituted linear or branched aliphatic group, wherein at least one hydrogen of R1 has been substituted with a halide, wherein the halide is fluorine.
  7. The sensor compound of claim 5, wherein either: a. R1 comprises an ether group, a heterocycle group, an amine group, or an amide group; b. at least one of R3-R10 is not hydrogen; or c. at least two of R3-R10 are a halide.
  8. A sensor device for detecting a target analyte, comprising: a substrate; and a sensor compound according to claim 5 to 7 positioned on the substrate in a plurality of detection zones, wherein said sensor compound having a nanofiber structure.
  9. The sensor device of claim 8, a. wherein at least one of the plurality of detection zones comprises a separately addressable electrode pair; b. wherein the substrate includes a plurality of holes allowing fluid flow through the substrate; c. further comprising a housing having an inlet and an outlet, wherein the substrate is positioned between the inlet and the outlet; d. further comprising a light source operably positioned to illuminate at least one of the plurality of detection zones; e. further comprising a fluorescence detector; f. wherein at least two of the plurality of detection zones comprise different sensor compounds; g. wherein at least two of the plurality of detection zones comprise different sensor compounds, wherein one or both of the different sensor compounds has a structure according to Formula II; or h. wherein the sensor compound forms a porous film.

Description

RELATED APPLICATION(S) This application claims priority to U.S. Provisional Application No. 62/190,609, filed July 9, 2015. GOVERNMENT INTEREST This invention was made with government support under 2009-ST-108-LR0005 awarded by the U.S. Department of Homeland Security. The government has certain rights in the invention. BACKGROUND Development of sensors or probes that can be used to detect fluid analytes is an active research field in chemistry and materials science. Detection of some fluid analytes is not only critical to air pollution monitoring and control, but also may provide expedient ways for quality control of food and even medical diagnosis of certain types of disease. However, detection of some fluid analytes can be challenging, largely due to the limited availability of sensory materials that facilitate detection with both high sensitivity and selectivity. One dimensional (1D) nanostructures represent attractive building blocks for some sensors and probes for fluid detection. Most of these nanodevices are fabricated from inorganic nanowires and carbon nanotubes. Some 1D organic nanomaterials have also been demonstrated, most of which are p-type semiconductor materials due to the limited availability of air-stable n-type organic materials. Liu Xiaoling, et al. (2015) "Nanocoiled Assembly of Asymmetric Perylene Diimides: Formulation of Structural Factors", The Journal of Physical Chemistry C, 119(11): 6446-6452 discloses asymmetric perylene diimides suitable for applications in areas such as optoelectronics, fluorescent sensors, and biological imaging. SUMMARY The current disclosure is directed to sensor compounds and associated methods and devices. In one example, a method of detecting a non-explosive analyte is disclosed. The method can include exposing a sensor compound to a non-explosive analyte and displaying a change in the sensor compound upon exposure of the sensor compound to the non-explosive analyte. The sensor compound can be selected from a group of compounds. In one example, the compound can have a structure according to Formula I: where R1, R2, and R3 are independently chosen from C1-C20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, and where R4-R11 are independently chosen from hydrogen, halides, carboxyl groups, hydroxyl groups, nitrile groups, C1-C8 alkyl groups, and combinations thereof. In another example, the sensor compound can have a structure according to Formula II: where R1 and R2 are independently chosen from C1-C20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, and where R3-R10 are independently chosen from hydrogen, halides, carboxyl groups, hydroxyl groups, nitrile groups, C1-C8 alkyl groups, and combinations thereof. In yet another example, the sensor compound can have a structure according to Formula III: where R1 is chosen from C1-C20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, and where R2-R9 are independently chosen from hydrogen, halides, carboxyl groups, hydroxyl groups, nitrile groups, C1-C8 alkyl groups, and combinations thereof. In some examples, combinations of the above recited compounds can be used in the method. The current disclosure also provides sensor compounds for detecting a target analyte. The sensor compounds can include compounds having a structure according to Formula I: where R1, R2, and R3 are independently chosen from C1-C20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, and where R4-R11 are independently chosen from hydrogen, halides, carboxyl groups, hydroxyl groups, nitrile groups, C1-C8 alkyl groups, and combinations thereof. In some examples, the sensor compound can have a structure according to Formula II: where R1 is chosen from C2-C20 substituted or unsubstituted linear aliphatic groups, branched aliphatic groups, cyclic groups, and aryl groups, where R2 includes a C2-C10 substituted or unsubstituted linear aliphatic group, an alkylbenzene group, a heterocycle, an aryl compound having an oxygen-containing side group, an aryl compound having a nitrogen-containing side group, an aryl compound having a sulfur-containing side group, or a combination thereof, and where R3-R10 are independently chosen from hydrogen, halides, carboxyl groups, hydroxyl groups, nitrile groups, C1-C8 alkyl groups, and combinations thereof. The current disclosure also describes a sensor device for detecting a target analyte. The sensor device can include a substrate and a nanofiber sensor material positioned on the substrate in a plurality of detection zones. The nanofiber sensor material can include a sensor compound as described above. Further, the sensor compound can have a nanofiber structure. There has thus been outlined, rather broadly, the more important features of the disclosure so tha