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WO2005021150A2 - Matieres polymeres marquees - Google Patents

Matieres polymeres marquees Download PDF

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Publication number
WO2005021150A2
WO2005021150A2 PCT/GB2004/003689 GB2004003689W WO2005021150A2 WO 2005021150 A2 WO2005021150 A2 WO 2005021150A2 GB 2004003689 W GB2004003689 W GB 2004003689W WO 2005021150 A2 WO2005021150 A2 WO 2005021150A2
Authority
WO
WIPO (PCT)
Prior art keywords
bead
polymer
ligand
moiety
nanoparticle
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB2004/003689
Other languages
English (en)
Other versions
WO2005021150A3 (fr
Inventor
Paul O'brien
Nigel L. Pickett
Andrew J. Sutherland
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Manchester
Original Assignee
University of Manchester
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0320384A external-priority patent/GB0320384D0/en
Priority claimed from GB0320471A external-priority patent/GB0320471D0/en
Application filed by University of Manchester filed Critical University of Manchester
Publication of WO2005021150A2 publication Critical patent/WO2005021150A2/fr
Publication of WO2005021150A3 publication Critical patent/WO2005021150A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B70/00—Tags or labels specially adapted for combinatorial chemistry or libraries, e.g. fluorescent tags or bar codes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0046—Sequential or parallel reactions, e.g. for the synthesis of polypeptides or polynucleotides; Apparatus and devices for combinatorial chemistry or for making molecular arrays
    • 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
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B50/00—Methods of creating libraries, e.g. combinatorial synthesis
    • C40B50/14—Solid phase synthesis, i.e. wherein one or more library building blocks are bound to a solid support during library creation; Particular methods of cleavage from the solid support
    • C40B50/16—Solid phase synthesis, i.e. wherein one or more library building blocks are bound to a solid support during library creation; Particular methods of cleavage from the solid support involving encoding steps
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/00497—Features relating to the solid phase supports
    • B01J2219/005—Beads
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/0054—Means for coding or tagging the apparatus or the reagents
    • B01J2219/00545—Colours
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/0054—Means for coding or tagging the apparatus or the reagents
    • B01J2219/00572—Chemical means
    • B01J2219/00576—Chemical means fluorophore

Definitions

  • the present invention relates to labelled polymeric materials and more paticularly to polymeric beads labelled with at least one nanoparticle.
  • the present invention provides a polymeric bead labelled with at least one nanoparticle associated with a moiety which is covalently incorporated in the polymer of the bead.
  • Beads in accordance with the invention may for example have a maximum cross- sectional size of 30 to 70 microns (e.g. about 50 microns) and may or may not be spherical.
  • Beads in accordance with the invention may incorporate a single nanoparticle or a plurality of nanoparticles.
  • the moiety (which is covalently incorporated in the polymer of the bead) is preferably a ligand for the nanoparticle and is most preferably a phosphine oxide ligand.
  • the polymer of the bead may be an addition polymer.
  • the polymer of the bead is an addition polymer and that the moiety (e.g. a ligand as aforesaid), prior to its covalent incorporation in the polymer of the bead, included at least one ethylenically unsaturated double bond.
  • the addition polymer may for example be comprised of styrene and/or divinylbenzene residues.
  • the preferred ligand employed in the invention is a phosphine oxide of the formula P(0)R 1 R 2 R 3 where R 1 ⁇ R 2 and R 3 are the same or different hydrocarbyl groups, at least one of which, prior to covalent incorporation of the ligand into the polymer of the bead, included at least one ethylenically unsaturated double bond.
  • the bead may incorporate reactive groups (e.g. functional groups) and may be used in solid phase organic synthesis, e.g. in combinatorial synthesis.
  • Polymeric beads as contemplated by the invention may be used as optically encoded solid supports in solid phase organic chemistry.
  • the beads may be produced by a suspension polymerisation technique.
  • a preferred such technique employs a monomer mixture comprised of the nanoparticle associated with a ligand of the formula P(0) R ls R and R 3 are as defined above and at least one of styrene and/or divinyl benzene.
  • the nanoparticles may be nanocrystals, e.g. quantum dots. Nanoparticles for use in the invention may for example be produced as disclosed in US-B-6 379 635. The nanoparticle may be a CdSe quantum dot.
  • the invention also provides nanoparticles associated with a moiety having a polymerisable group (e.g. an ethylenically unsaturated group).
  • the moiety may be a ligand as described above.
  • Fig. 1 schematically illustrates preparation of resin beads from a mixture of styrene, divinylbenzene and a quantum dot (QD) material associated with a ligand incorporating ethylenically unsaturated groups
  • Fig. 2 illustrates fluorescent emission finge rinting of quantum dot-containing polymer beads
  • Quantum dots were synthesised from (Li )[Cd 10 Se 4 (SPh) 16 ] and hexadecylamine as described previously 9 to give CdSe core particles capped with hexadecylamine. Ligand exchange was then performed to displace the hexadecylamine with one of two polymerisable ligands 1 or 5 (Scheme 1) ⁇ ' 8 ' 10 .
  • the structure of each of the ligands is based on the commonly used quantum dot capping agent trioctylphosphine oxide (TOPO) 2, since TOPO has a good affinity for CdSe quantum dots. Success of ligand exchange was confirmed by 1H NMR and by observing the increase in solubility of the coated quantum dots in styrene. Polymerisable ligand 1 was synthesised using the two-step protocol described by
  • Emrick et al ' and a variation of this route was used to construct ligand 5 (Scheme 1). Specifically, dibutylphosphite 3 was converted into dioctylphosphine oxide 4 by treatment with octylmagnesium bromide followed by an aqueous acid quench. A subsequent sodium hydride mediated alkylation step
  • Table 1 Compositions of quantum dot-containing beads generated using the small- scale suspension polymerisation procedure.
  • Quantum dots 20mg, prepared according to a previously published procedure 9 , were dissolved in 1,4-dioxane, 4ml, containing a large excess of the polymerisable ligand, 1 mmol. The solution was then stirred for 20 hours at room temperature. Centrifugation and drying resulted in ligand exchanged quantum dots (14mg for the p- vinylbenzylDOPO and lOmg for p-octenylDOPO batches).
  • Aqueous polvinylalcohol (PVA) solution (20ml, 1% wt/wt, 87-89% hydrolyzed PVA, average MW 85,000-146,000) was prepared and transferred to the reaction vessel (screw cap boiling tube attached to a N 2 /vacuum manifold system) and degassed with N for 20 minutes.
  • a monomer mixture - styrene (10 mmol), divinylbenzene and quantum dots (Table 1) - was prepared and stirred for 5 minutes.
  • ALBN (76 ⁇ mol) was added to the monomer mixture then the resultant mixture was stirred for a further 15 minutes with N 2 degassing.
  • the dark orange monomer solution (colour due to the quantum dots) was added to the PVA solution while rapidly stirring with a cross-shaped magnetic stirrer.
  • a two phase system resulted with orange droplets being suspended in the uncoloured aqueous PVA solution.
  • the suspension was stirred at room temperature for 30 minutes before the temperature was increased to 70°C and stirring was continued for a further 4 hours.
  • the resin beads were then collected over a 38 ⁇ a sieve and washed in situ with copious amounts of water.
  • the damp beads were then transferred to a sintered funnel and washed with methanol (100 cm 3 ), MeOH/THF, 1/1 (100 cm 3 ), THF (100 cm 3 ), CH 2 C1 2 (100 cm 3 ) and acetone (100 cm 3 ).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Structural Engineering (AREA)
  • Composite Materials (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un cordon polymère marqué avec au moins une nanoparticule associée à un groupe fonctionnel incorporé par covalence dans le polymère du cordon. Dans un mode de réalisation préféré, ce groupe fonctionnel est un ligand de la nanoparticule et de préférence un ligand d'oxyde de phosphine.
PCT/GB2004/003689 2003-09-01 2004-08-27 Matieres polymeres marquees Ceased WO2005021150A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB0320384A GB0320384D0 (en) 2003-09-01 2003-09-01 Labelled polymeric materials
GB0320384.1 2003-09-01
GB0320471A GB0320471D0 (en) 2003-09-02 2003-09-02 Labelled polymeric materials
GB0320471.6 2003-09-02

Publications (2)

Publication Number Publication Date
WO2005021150A2 true WO2005021150A2 (fr) 2005-03-10
WO2005021150A3 WO2005021150A3 (fr) 2005-04-21

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PCT/GB2004/003689 Ceased WO2005021150A2 (fr) 2003-09-01 2004-08-27 Matieres polymeres marquees

Country Status (1)

Country Link
WO (1) WO2005021150A2 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7544725B2 (en) 2006-04-05 2009-06-09 Nanoco Technologies Limited Labelled beads
US7588828B2 (en) 2004-04-30 2009-09-15 Nanoco Technologies Limited Preparation of nanoparticle materials
US7803423B2 (en) 2004-04-30 2010-09-28 Nanoco Technologies Limited Preparation of nanoparticle materials
US7867556B2 (en) 2005-10-28 2011-01-11 Nanoco Technologies Limited Controlled preparation of nanoparticle materials
US7867557B2 (en) 2005-08-12 2011-01-11 Nanoco Technologies Limited Nanoparticles
CN102272217A (zh) * 2008-11-04 2011-12-07 纳米技术有限公司 表面功能化的纳米颗粒
JP2011530187A (ja) * 2008-08-07 2011-12-15 ナノコ テクノロジーズ リミテッド 表面官能化ナノ粒子
US8337720B2 (en) 2008-02-25 2012-12-25 Nanoco Technologies, Ltd. Semiconductor nanoparticle capping agents
US8394663B2 (en) 2007-04-25 2013-03-12 Nanoco Technologies, Ltd. Hybrid photovoltaic cells and related methods
US8563348B2 (en) 2007-04-18 2013-10-22 Nanoco Technologies Ltd. Fabrication of electrically active films based on multiple layers
US8741177B2 (en) 2008-07-19 2014-06-03 Nanoco Technologies Ltd. Method for producing aqueous compatible nanoparticles
US8784701B2 (en) 2007-11-30 2014-07-22 Nanoco Technologies Ltd. Preparation of nanoparticle material
US8859442B2 (en) 2010-04-01 2014-10-14 Nanoco Technologies Ltd. Encapsulated nanoparticles
US8921827B2 (en) 2008-11-19 2014-12-30 Nanoco Technologies, Ltd. Semiconductor nanoparticle-based light-emitting devices and associated materials and methods
US8957401B2 (en) 2009-09-23 2015-02-17 Nanoco Technologies, Ltd Semiconductor nanoparticle-based materials
CN105062462A (zh) * 2015-07-13 2015-11-18 京东方科技集团股份有限公司 发光复合物、发光材料、显示用基板及制备方法、显示装置
CN116814106A (zh) * 2023-07-05 2023-09-29 广东红海湾发电有限公司 一种耐高温阻燃光伏电缆用荧光标记材料及其制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0916699D0 (en) 2009-09-23 2009-11-04 Nanoco Technologies Ltd Semiconductor nanoparticle-based materials

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005508493A (ja) * 2001-06-28 2005-03-31 アドヴァンスト リサーチ アンド テクノロジー インスティテュート、インコーポレイティッド 多色量子ドット標識ビーズおよびそのコンジュゲートの製造方法

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8524365B2 (en) 2004-04-30 2013-09-03 Nanoco Technologies Ltd. Preparation of nanoparticle materials
US7803423B2 (en) 2004-04-30 2010-09-28 Nanoco Technologies Limited Preparation of nanoparticle materials
US7985446B2 (en) 2004-04-30 2011-07-26 Nanoco Technologies Limited Preparation of nanoparticle materials
US8062703B2 (en) 2004-04-30 2011-11-22 Nanoco Technologies Ltd. Preparation of nanoparticle materials
US7588828B2 (en) 2004-04-30 2009-09-15 Nanoco Technologies Limited Preparation of nanoparticle materials
US7867557B2 (en) 2005-08-12 2011-01-11 Nanoco Technologies Limited Nanoparticles
US7867556B2 (en) 2005-10-28 2011-01-11 Nanoco Technologies Limited Controlled preparation of nanoparticle materials
US7674844B2 (en) 2006-04-05 2010-03-09 Nanoco Technologies Limited Labelled beads
US7544725B2 (en) 2006-04-05 2009-06-09 Nanoco Technologies Limited Labelled beads
US8563348B2 (en) 2007-04-18 2013-10-22 Nanoco Technologies Ltd. Fabrication of electrically active films based on multiple layers
US8394663B2 (en) 2007-04-25 2013-03-12 Nanoco Technologies, Ltd. Hybrid photovoltaic cells and related methods
US9251922B2 (en) 2007-11-30 2016-02-02 Nanoco Technologies, Ltd. Preparation of nanoparticle material
US8784701B2 (en) 2007-11-30 2014-07-22 Nanoco Technologies Ltd. Preparation of nanoparticle material
US8337720B2 (en) 2008-02-25 2012-12-25 Nanoco Technologies, Ltd. Semiconductor nanoparticle capping agents
US8741177B2 (en) 2008-07-19 2014-06-03 Nanoco Technologies Ltd. Method for producing aqueous compatible nanoparticles
US8597730B2 (en) 2008-08-07 2013-12-03 Nanoco Technologies Ltd. Surface functionalised nanoparticles
JP2011530187A (ja) * 2008-08-07 2011-12-15 ナノコ テクノロジーズ リミテッド 表面官能化ナノ粒子
US8394976B2 (en) 2008-11-04 2013-03-12 Nanoco Technologies, Ltd. Surface functionalised nanoparticles
JP2012507588A (ja) * 2008-11-04 2012-03-29 ナノコ テクノロジーズ リミテッド 表面官能化ナノ粒子
CN102272217A (zh) * 2008-11-04 2011-12-07 纳米技术有限公司 表面功能化的纳米颗粒
US8921827B2 (en) 2008-11-19 2014-12-30 Nanoco Technologies, Ltd. Semiconductor nanoparticle-based light-emitting devices and associated materials and methods
US8957401B2 (en) 2009-09-23 2015-02-17 Nanoco Technologies, Ltd Semiconductor nanoparticle-based materials
US8859442B2 (en) 2010-04-01 2014-10-14 Nanoco Technologies Ltd. Encapsulated nanoparticles
US9159590B2 (en) 2010-04-01 2015-10-13 Nanoco Technologies, Ltd. Encapsulated nanoparticles
CN105062462A (zh) * 2015-07-13 2015-11-18 京东方科技集团股份有限公司 发光复合物、发光材料、显示用基板及制备方法、显示装置
EP3255117A4 (fr) * 2015-07-13 2018-07-25 BOE Technology Group Co., Ltd. Complexe luminescent, matériau luminescent, substrat d'affichage, procédé de préparation et dispositif d'affichage
US10287498B2 (en) 2015-07-13 2019-05-14 Boe Technology Group Co., Ltd. Luminescent complex, luminescent material, substrate for display and production method thereof, and display apparatus
CN116814106A (zh) * 2023-07-05 2023-09-29 广东红海湾发电有限公司 一种耐高温阻燃光伏电缆用荧光标记材料及其制备方法

Also Published As

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