US20110269240A1 - Immobilizing chemical or biological sensing molecules on semi-conducting nanowires - Google Patents

Immobilizing chemical or biological sensing molecules on semi-conducting nanowires Download PDF

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US20110269240A1
US20110269240A1 US10/795,730 US79573004A US2011269240A1 US 20110269240 A1 US20110269240 A1 US 20110269240A1 US 79573004 A US79573004 A US 79573004A US 2011269240 A1 US2011269240 A1 US 2011269240A1
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chemical
biological
semi
biological sensor
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US8048377B1 (en
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Zhang-Lin Zhou
Zhiyong Li
Sean Xiao-An Zhang
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Hewlett Packard Development Co LP
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54366—Apparatus specially adapted for solid-phase testing
    • G01N33/54373—Apparatus specially adapted for solid-phase testing involving physiochemical end-point determination, e.g. wave-guides, FETS, gratings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/734—Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc.
    • Y10S977/742—Carbon nanotubes, CNTs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/734—Fullerenes, i.e. graphene-based structures, such as nanohorns, nanococoons, nanoscrolls or fullerene-like structures, e.g. WS2 or MoS2 chalcogenide nanotubes, planar C3N4, etc.
    • Y10S977/742—Carbon nanotubes, CNTs
    • Y10S977/745—Carbon nanotubes, CNTs having a modified surface
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S977/00—Nanotechnology
    • Y10S977/84—Manufacture, treatment, or detection of nanostructure
    • Y10S977/842—Manufacture, treatment, or detection of nanostructure for carbon nanotubes or fullerenes

Definitions

  • a chemical or biological sensor can comprise a semi-conducting nanowire and a chemical or biological sensing molecule tethered to the semi-conducting nanowire through a spacer group including a hydrophilic reactive group.
  • a chemical or biological sensor can comprise an array of semi-conducting nanowires, electrical leads that provide an electrical property to the array, and a signal measurement apparatus electrically coupled to the array and configured for detecting changes in the electrical property, which can be electrical current carried by the array.
  • the array can include individual semi-conducting nanowires, each including chemical or biological sensing molecules tethered thereto through a spacer group including a hydrophilic reactive group.
  • a method of detecting the presence of an analyte in an environment can comprise multiple steps.
  • One such step includes applying an electrical current along a nanowire sensing element of a chemical or biological sensor, wherein the nanowire sensing element includes a semi-conducting nanowire and a chemical or biological sensing molecule tethered to the semi-conducting nanowire through a spacer group including a hydrophilic reactive group.
  • Additional steps can include exposing the nanowire sensing element to an environment suspected of containing an analyte that is interactive with the chemical or biological sensing molecule, and determining whether the conductance is altered as a result of the analyte interacting with the chemical or biological sensing molecule.
  • nanowire includes elongated structures of semi-conducting material, such as silicon, germanium, gallium arsenide, tin oxide, cadmium sulfide, cadmium telluride, cadmium selenide, or the like, which have a narrow cross-section, e.g., less than 100 nm.
  • the nanowires can have an aspect ratio (length to width) that is greater than about 5. In other words, nanowires are generally elongated by at least five times along an axis with respect to other perpendicular axes.
  • nanowire does not imply that the structure must be wire-like, only that the structure is elongated along one of its axes.
  • nanowires structures that are wire-like, tubular, rope-like, or belt-like are considered to be nanowires. More specifically, traditional nanowires, nanotubes, nanoropes, and nanobelts are all considered to be nanowires in accordance with embodiments of the present invention. Additionally, a specific reference to a type of material does not imply that a single compositional component is necessarily present.
  • a “silicon nanowire” can include a traditional nanowire, nanotube, nanorope, or nanobelt that can be primarily or totally silicon, or can be a composite or hybrid nanowire, such as a boron-doped silicon nanowire, nanotube, nanorope, or nanobelt.
  • Semi-conducting nanowires can be prepared by one of several methods, such as by growing methods or by fabrication methods wherein e-beam lithographic or nanoimprinting methods are used to form the nanowire.
  • e-beam lithographic or nanoimprinting methods are used to form the nanowire.
  • the use of chemical vapor deposition on catalyst nanoparticles as a nucleation site can be used.
  • well-controlled sizes, patterns, and/or densities of nanowires can be grown in an array.
  • These nanowires can remain attached to the substrate and used as a chemical or biological sensor, or can be harvested for inclusion in a chemical or biological sensor.
  • nanowires include template assistance methods, electrochemical deposition methods, high pressure injection methods, chemical vapor deposition methods, and laser assisted methods, each of which is generally known in the art.
  • template assistance methods electrochemical deposition methods, high pressure injection methods, chemical vapor deposition methods, and laser assisted methods, each of which is generally known in the art.
  • individual semi-conducting nanowires can be from about 10 nm to 100 nm in width.
  • analyte shall mean a substance that may be present in a fluid, gas or solid state environment that is being tested for using the chemical or biological sensing molecule-modified semi-conducting nanowires of the present invention.
  • the analyte can be a chemical or of a chemical class, or can be a biological substance or of a biological class.
  • electrical property includes properties commonly known in the electrical arts, such as current, capacitance, voltage, resistance, etc.
  • lower when referring to alkyl groups, alkoxy groups, or the like, includes compositions having a C 1 -C 4 carbon chain, e.g., methyl, methoxy, ethyl, ethoxy, propyl, isopropyl, butyl, isobutyl, etc.
  • a size range of about 1 ⁇ m to about 200 ⁇ m should be interpreted to include not only the explicitly recited limits of 1 ⁇ m and about 200 ⁇ m, but also to include individual sizes such as 2 ⁇ m, 3 ⁇ m, 4 ⁇ m, and sub-ranges such as 10 ⁇ m to 50 ⁇ m, 20 ⁇ m to 100 ⁇ m, etc.
  • a chemical or biological sensor can comprise a semi-conducting nanowire and a chemical or biological sensing molecule tethered to the semi-conducting nanowire through a spacer group including a hydrophilic reactive group.
  • a chemical or biological sensor can comprise an array of semi-conducting nanowires, electrical leads that provide an electrical current to the array, and a signal measurement apparatus electrically coupled to the array and configured for detecting changes in the electrical current carried by the array.
  • the array can include individual semi-conducting nanowires, each including chemical or biological sensing molecules tethered thereto through a spacer group including a hydrophilic reactive group.
  • a method of detecting the presence of an analyte in an environment can comprise multiple steps.
  • One such step includes applying a voltage or current along a nanowire sensing element of a chemical or biological sensor, wherein the nanowire sensing element includes a semi-conducting nanowire and a chemical or biological sensing molecule tethered to the semi-conducting nanowire through a spacer group including a hydrophilic reactive group.
  • Additional steps can include exposing the nanowire sensing element to an environment suspected of containing an analyte that is interactive with the chemical or biological sensing molecule, and determining whether the current is altered as a result of the analyte interacting with the chemical or biological sensing molecule.
  • chemical or biological sensing molecules can be attached to the surface of the semi-conducting nanowires to form a functionality that can be configured to sense the presence of an analyte.
  • a current can be applied to a semi-conducting nanowire including an attached chemical or biological sensing molecule.
  • the nanowire can also be electrically coupled to a sensing device that can detect minimal changes in current. In one example, changes on the order of Pico amperes can be detected.
  • the chemical or biological sensing molecule interacts or reacts with a predetermined analyte, the conductance of the nanowire can change, which can be detected by the sensing device.
  • the nanowires can be configured such that two locations of the nanowire are attached to electrical leads to apply the current.
  • the nanowire can be a freestanding nanowire of an array of freestanding nanowires, which can also be used as a chemical or biological sensor.
  • the chemical or biological sensing molecules can be used for detecting chemical or biological substances/agents, such as metal ions, peptides, proteins, nucleic acids, enzymes, antibodies, and/or pathogens. These materials can be adapted for use in an aqueous or organic solution or dispersion, and can also be adapted for use in solid state or gaseous environments. For example, by immobilizing a fluorescent probe on a semi-conducting nanowire, gaseous or solid environment sensing can be realized.
  • a practical chemical process for immobilizing chemical or biological sensing molecules onto a semi-conducting nanowire.
  • a silicon nanowire by treating a silicon nanowire with certain chemical reagents, such as 3-aminopropyltriethoxysilane or tetrachlorosilane, one can introduce a reactive group onto the semi-conducting nanowire.
  • the reactive group can be configured to be reactive with a chemical or biological sensing molecule to form a stable covalent bond between silicon surface and the molecular sensing molecule.
  • the reaction should be controlled such that at least one sensing moiety of the sensing molecule is free to interact with the environment.
  • the attachment mechanism should not destroy a functionality of the sensing moiety of the molecule used to modify the semi-conducting nanowire surface.
  • the chemical or biological sensing molecule can be firmly attached to the silicon surface via a covalent bond, allowing for detection of chemical reagents and/or biological species in an environment.
  • the nano-scale chemical or biological sensors prepared can be well suited for use in liquid environments, gaseous environments, and in solid state applications.
  • NW is a semi-conducting nanowire (including traditional nanowires, nanotubes, nanoropes, and nanobelts)
  • B is a bridging group
  • A is an spacer group
  • M is a chemical or biological sensing molecule.
  • the chemical or biological sensing molecule (M) can include a potential sensing molecular unit, such as those used as ion indicators, pH indicators, DNA stains, protein stains, enzyme indicators, etc.
  • the sensing molecule can be a fluorescent dye, which can include, but is not limited to 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye, fluorescein and substituted fluorescein dye, rhodamine and substituted rhodamine dye, coumarin and substituted coumarin dye, naphthalene and substituted naphthalene dye, pyrene and substituted pyrene dye, pyridyloxazole dye, 7-nitrobenz-2-oxa-1,3-diazole derivative dyes, anthracene and substituted anthracene derivative dyes, eosin and erythrosine derivative dyes, and photochromic dyes.
  • a chemical or biological sensing molecule is a crown ether configured for detection of metal ions.
  • an 18-crown-6 molecule can be attached to a silicon nanowire.
  • the metal ions can complex or chelate with the crown ether, resulting in a fluctuation of the conductance.
  • the conductance can be extremely sensitive to the change of the nanowire surface properties.
  • any bridging group (B) that can act to bridge the semi-conducting nanowire to the chemical or biological sensing molecule (through the spacer group) can be used in accordance with the present invention.
  • the bridging group, prior to attachment to the semi-conducting nanowire, typically includes a reactive moiety that is reactive with the semi-conducting nanowire.
  • Exemplary reactive moieties of the bridging group include those having the formula SiR 3 , where each R can independently be halo, lower alkoxy, or a lower alkyl group (such as methyl, ethyl, propyl, or iso-propyl), with the proviso that at least one R must be reactive with the semi-conducting nanowire, e.g., halo or lower alkoxy.
  • Halo and lower alkoxy are exemplary groups that are reactive for attachment to a silicon surface.
  • Other reactive mechanisms can also be used, such as triflates, acyl, oximes, or amines, for example.
  • the bridging group (B) can be attached to a spacer group (A) that can be used to tether the chemical or biological sensing molecule to the reactive group (and ultimately, to the semi-conducting nanowire surface).
  • the spacer group which includes a hydrophilic reactive group that more polar than a carbon-containing moiety to which it is attached, acts to separate the chemical or biological sensing molecule (M) from the surface of the nanowire to maximize the interaction between the chemical or biological sensing molecule (M) and desired chemical or biological substance being tested or analyzed.
  • the spacer group can include various combinations of alkyl, aryl, alkaryl, and aralkyl moieties, and also can include one or more hydrophilic moiety, i.e., more hydrophilic than the alkyl, aryl, alkaryl, or aralkyl moiety to which it is attached.
  • hydrophilic reactive groups include O, S, amine nitrogen, amide, alkylamide, sulfonyl, sulfonamide, or carbonyl functionalities, for example.
  • the alkyl, aryl and aralkyl moieties can also be substituted by —OH, —SH, —Cl, or the like.
  • the spacer group can include from about 3 to 10 carbon atoms.
  • Exemplary appropriate spacer groups can include:
  • each R can independently be halo, lower alkoxy, or a lower alkyl group (such as methyl, ethyl, propyl, or iso-propyl), with the proviso that at least one R must be reactive with the semi-conducting nanowire, e.g., halo or lower alkoxy.
  • Other reactive groups that might be used include triflates, acyl, oximes, or amines.
  • a halo silane reactive group and/or a lower alkyl silane reactive group can be present, as represented by —SiR 3 .
  • the semi-conducting nanowire is not shown in Formula 2, but can be reactive with one or more of the R groups, and at that point, the —SiR 3 portion of Formula 2 will become the bridging group.
  • a spacer group is also shown having the formula —(CH 2 ) b O(CH 2 ) a —, wherein a can be from 0 to 3, and b can be from 1 to 10.
  • the spacer group is shown attached to the chemical or biological sensing molecule. Though attached as shown, the chemical or biological sensing molecule should still maintain its functionality for interacting with potential environmental compositions desired to assay. Further, any means or point of attachment (through a spacer group or without a spacer group) between the chemical or biological sensing molecule and the reactive group can be used, provided at least a portion of the functionality of the chemical or biological sensing molecule can be maintained. Further, though a specific type of spacer group is shown, other spacer groups can be used, as would be known by one skilled in the art after reading the present disclosure.
  • the vertical line represents a semi-conducting nanowire and each R can independently be halo, lower alkoxy, or lower alkyl, e.g., methyl, ethyl, propyl, iso-propyl, etc., with the proviso that at least one R must be reactive with the semi-conducting nanowire, e.g., halo or lower alkoxy.
  • reactive groups other than halo or alkoxy can also be used.
  • the example shown in Formula 3 is a lower alkoxy example.
  • A is a spacer group and M is a chemical or biological sensing molecule.
  • the vertical line represents a semi-conducting nanowire
  • A′ represents a spacer group precursor that includes a moiety that is reactive with a chemical or biological sensing molecule
  • M′ represents a chemical or biological sensing molecule precursor that has a reactive moiety that is reactive with the reactive spacer group precursor
  • A-M represents the spacer group covalently attached to the chemical or biological sensing molecule.
  • the reactive moiety of A′ can be a leaving group or a nucleophile, and/or likewise, the reactive moiety of M′ can be either a leaving group or nucleophile, provided A′ is reactive with M′ to form the -A-M portion of the composition.
  • M is a chemical or biological sensing molecule and the vertical line is a semi-conducting nanowire.
  • the chemical or biological sensing molecule can be any of a number of chemical or biological sensing molecular units used as ion indicators, pH indicators, DNA stains, protein stains, enzyme indicators, etc. As shown, the chemical or biological sensing molecule can be treated with commercially available 3-(triethoxysilyl)propylamine, the reaction between the amino group with an activated ester group on the potential sensing molecular unit can occur to form a chemical or biological sensing molecule reagent.
  • the reagent can be reacted with the semi-conducting nanowire to form the chemical or biological sensing molecule-modified semi-conducting nanowire.
  • a chemical reaction between the triethoxysilyl group and the hydroxy group on the silicon surface can occur, forming a chemical bond, thus immobilizing the potential sensing molecular unit to the silicon substrate.
  • a tri(ethoxy)silylpropylamine which includes a silane group that is reactive with the semi-conducting nanowires, and further includes a reactive amino group is shown.
  • the reactive amino group is reactive with an active ester that is attached to a chemical or biological sensing molecule, as shown:
  • M is a chemical or biological sensing molecule and the vertical line is a semi-conducting nanowire. M can be any of a number of chemical or biological sensing molecular units used as ion indicators, pH indicators, DNA stains, protein stains, enzyme indicators, etc.
  • Photochromism can be defined as a reversible phototransformation of a chemical species between two forms. Each form can have different absorption spectra; different physicochemical properties such as refractive index, dielectric constant, and/or oxidation/reduction potential; and different geometrical structure. These molecular property changes can be applied to various photonic devices, which can be used to determine the presence of an analyte in an environment. The immobilization of chemical or biological sensing molecules on nanowires can enable such sensitivities.
  • Nanowires can be grown using conventional growth techniques, or can be fabricated using fabrication techniques. If grown, one of several methods can be used including chemical vapor deposition (CVD), nanoimprinting, nanotemplating, and/or electrodeposition, to name a few. Alternatively, other schemes for nanowire growth can be carried out as well. For example, nanowire growth material can be provided by ablating a solid target, such as with a laser. Such a method can be carried out with or without a substrate. In other embodiments, fabrication techniques can be carried out, such as high pressure injection methods, e-beam lithographic methods, and nanoimprinting methods.
  • CVD chemical vapor deposition
  • nanoimprinting nanotemplating
  • electrodeposition to name a few.
  • other schemes for nanowire growth can be carried out as well.
  • nanowire growth material can be provided by ablating a solid target, such as with a laser. Such a method can be carried out with or without a substrate.
  • fabrication techniques can be carried out, such as high pressure injection methods
  • Semi-conducting nanowires (1) are treated with 3-(triethoxysilyl)propylamine (2) to form surface modified nanowires (3).
  • Reactive Sc ester functionalized fluorescent calcium ion indicator compositions (4) which are reactive with the amine group of the 3-(triethoxyxilyl)propylamine are then used to treat the modified nanowires such that a covalent bond forms between the modified nanowires and the ion indicators.
  • This causes the ion indicators to become tethered to the semi-conducting nanowires such that the receptor unit faces generally away from the semi-conducting nanowires, thus forming fluorescent calcium ion indicator-attached semi-conducting nanowires (5).
  • the preparative scheme is shown generally below:
  • Semi-conducting nanowires (1) are treated with 3-(triethoxysilyl)propylamine (2) to form surface modified nanowires (3).
  • Spiropyran target compositions modified with reactive sucinimidyl group (6) that are reactive with the 3-(triethoxysilyl)propylamine are then used to treat the modified nanowires, forming a covalent bond between modified nanowires and the modified spiropyran target composition.
  • the resulting compositions formed are spiropyran target-attached semi-conducting nanowires (7a).
  • the compound undergoes an isomerization wherein the spiro inkage is severed, resulting in a highly polar “open” form (7b).
  • the immobilized spiropyran compound can be switched from a closed to open form with UV light, and from an open to closed form with visible light.
  • the reaction scheme of this preparation is shown below:
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