Luminescent hybrid nanomaterials with aggregation induced emission

Patent metadata

Field	Value
Publication number	US-2016362601-A1
Application number	US-201515120977-A
Country	US
Kind code	A1
Filing date	Feb 24, 2015
Priority date	Feb 24, 2014
Publication date	Dec 15, 2016
Grant date	—

Abstract

A luminescent hybrid nanomaterial comprising: at least one inorganic nanomaterial comprising an inorganic first compound; and at least one second compound comprising a first aggregation-induced emission moiety, wherein the at least one second compound is grafted on at least part of a surface of the inorganic first compound.

First claim

1 . A luminescent hybrid nanomaterial comprising:
at least one inorganic nanomaterial comprising an inorganic first compound; and at least one second compound comprising a first aggregation-induced emission moiety, wherein the at least one second compound is grafted on at least part of a surface of the inorganic first compound.

2 . The luminescent hybrid nanomaterial according to claim 1 , wherein the first aggregation-induced emission moiety comprises:
a first cyclic conjugated substituent; and a second substituent conjugated with the first cyclic conjugated substituent.

3 . The luminescent hybrid nanomaterial according to claim 2 , wherein the first cyclic conjugated substituent is selected from the group comprising an heterole, and a phenyl group.

4 . The luminescent hybrid nanomaterial according to claim 2 , further comprising a restricted intramolecular rotation of the second substituent with respect to the first cyclic conjugated substituent.

5 . The luminescent hybrid nanomaterial according to claim 2 , wherein the second substituent is cyclic.

6 . The luminescent hybrid nanomaterial according to claim 2 , wherein the first aggregation-induced emission moiety further comprises a first linking moiety selected from the group comprising an ether, a linear C1-C2 alkyl, C2 alkenyl and C2 alkynyl group, the first linking moiety connecting the first cyclic conjugated substituent to the second substituent.

7 . The luminescent hybrid nanomaterial according to claim 1 , wherein the at least one second compound has one of the following structures:

wherein:
M is selected from the group comprising Si, Ge, Sn and Pb;
M′ is selected from the group comprising P, As, Sb and Bi;
M″ is selected from the group comprising Si, Ge, Sn, Pb, P, As, Sb and Bi;
X is selected from the group comprising H, OH SH, SeH and TeH, or X is selected from the group comprising OR′, SR′, SeR′ and TeR′,
R′ being a first linker, the first linker comprising a first anchoring group,
the first linker being a linear, cyclic or branched, saturated or unsaturated, C1-C20 alkyl group,
the first anchoring group being selected from the group comprising a hydroxyl, thiol, carboxylic acid, carboxylic acid ester, cyano, amino, amido, sulfinic acid, sulfonic acid, phosphonic acid, dithiophosphinic acid, phosphate, phosphoester, phosphothioester, phosphine oxide, phosphine sulfide, phosphine, and silanol group;
Y is selected from the group comprising O, S, Se and Te;
R1 is selected from the group comprising a cyano, amino, amido, carboxylic acid, polyethylene glycol, polypropylene glycol, C1-C20 alkyl, C2-C20 alkenyl, a C2-C20 alkynyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C1-C20 alkylamido, C2-C20 heteroalkyl, C1-C20 haloalkyl, C6-C20 aryl, C4-C20 heteroaryl, C7-C20 alkylaryl, C7-C20 arylalkyl, C8-C20 arylalkenyl, C8-C20 arylalkynyl, C6-C20 haloaryl, C2-C20 alkylketone, C2-C20 alkylthione, C2-C20 alkylcarbonate, C2-C20 carboxylic acid ester, C1-C20 alkylsulfinic acid, C1-C20 alkylsulfonic acid, C1-C20 alkylphosphonic acid, C1-C20 alkyldithiophosphinic acid, C1-C20 alkylphosphate, C1-C20 alkylphosphoester, C1-C20 alkylphosphine oxide, and C1-C20 alkylphosphine group; or R1 and is selected from the group comprising H, OH SH, SeH and TeH, or R1 is selected from the group comprising OR″, SR″, SeR″ and TeR″, R″ being a second linker comprising a second anchoring group,
the second linker being a linear, cyclic or branched, saturated or unsaturated, C1-C20 alkyl group,
the second anchoring group being selected from the group comprising a hydroxyl, thiol, carboxylic acid, carboxylic acid ester, cyano, amino, amido, sulfinic acid, sulfonic acid, phosphonic acid, dithiophosphinic acid, phosphate, phosphoester, phosphothioester, phosphine oxide, phosphine sulfide, phosphine, and silanol group; and
each R2 to R6 is independently selected from the group comprising a hydrogen, hydroxy, nitro, nitroxy, nitroso, halide, cyano, isothiocyanato, amino, amido, imino, azido, cyanato, isocyanato, polyethylene glycol, polypropylene glycol, C1-C20 alkyl, C2-C20 alkenyl, a C2-C20 alkynyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C1-C20 alkylamido, C2-C20 heteroalkyl, C1-C20 haloalkyl, C6-C20 aryl, C4-C20 heteroaryl, C7-C20 alkylaryl, C7-C20 arylalkyl, C8-C20 arylalkenyl, C8-C20 arylalkynyl, C6-C20 haloaryl, C2-C20 alkylketone, C2-C20 alkylthione, C2-C20 alkylcarbonate, carboxylic acid, C2-C20 carboxylic acid ester, sulfinic acid, C1-C20 alkylsulfinyl, sulfonic acid and C1-C20 alkylsulfonyl group.

8 . The hybrid nanomaterial according to claim 7 , wherein R2 and R3, or R3 and R4, or R4 and R5, or R5 and R6 form together a ring system.

9 . The hybrid nanomaterial according to claim 7 , wherein the at least one second compound has one of the following structures:

10 . The luminescent hybrid nanomaterial according to claim 1 , wherein the at least one second compound has the following structure:

wherein:
R7 is a second linker comprising a first anchoring group, the second linker being a linear, cyclic or branched, saturated or unsaturated, C1-C20 alkyl group,
the first anchoring group being selected from the group comprising a hydroxyl, thiol, carboxylic acid, carboxylic acid ester, cyano, amino, amido, sulfinic acid, sulfonic acid, phosphonic acid, dithiophosphinic acid, phosphate, phosphoester, phosphothioester, phosphine oxide, phosphine sulfide, phosphine, and silanol group; and
each R8 to R10 is independently selected from the group comprising a hydrogen, hydroxy, nitro, nitroxy, nitroso, halide, cyano, isothiocyanato, amino, amido, imino, azido, cyanato, isocyanato, polyethylene glycol, polypropylene glycol, C1-C20 alkyl, C2-C20 alkenyl, a C2-C20 alkynyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylamino, C1-C20 alkylamido, C2-C20 heteroalkyl, C1-C20 haloalkyl, C6-C20 aryl, C4-C20 heteroaryl, C7-C20 alkylaryl, C7-C20 arylalkyl, C8-C20 arylalkenyl, C8-C20 arylalkynyl, C6-C20 haloaryl, C2-C20 alkylketone, C2-C20 alkylthione, C2-C20 alkylcarbonate, carboxylic acid, C2-C20 carboxylic acid ester, sulfinic acid, C1-C20 alkylsulfinyl, sulfonic acid and C1-C20 alkylsulfonyl group.

11 . The hybrid nanomaterial according to claim 10 , wherein the at least one second compound has the following structure:

12 . The hybrid nanomaterial according to claim 1 , wherein the at least one second compound further comprises a second aggregation-induced emission moiety and/or a third substituent, which is an additional cyclic conjugated moiety, and/or at least one additional substituent selected from the group comprising a solubilizing moiety, a self assembly group, a chiral group, an oligomer and a polymer.

13 . A process of manufacture of a luminescent hybrid nanomaterial according to claim 1 , the process comprising:
providing the at least one inorganic nanomaterial comprising the inorganic first compound; providing the at least one second compound; and contacting the at least one second compound to at least part of the surface of the inorganic first compound, under conditions appropriate to graft or physisorb the at least one second compound on the

Assignees

• Centre Nat Rech Scient
• Université Aix-Marseille
• Université De Rennes 1

Inventors

• Ackermann Jörg
• Margeat Olivier
• Hissler Muriel
• Bouit Pierre Antoine

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• Y10S977/95

  Electromagnetic energy · CPC title

• Y10S977/89

  Deposition of materials, e.g. coating, cvd, or ald · CPC title

• B82Y20/00

  Nanooptics, e.g. quantum optics or photonic crystals · CPC title