Highly Emissive Far-Red/Near-Infrared Fluorescent Conjugated Polymer-Based Nanoparticles
AssigneeNational University of Singapore
InventorsBin Liu, Jie Liu, Dan Ding, Junlong Geng, Lun-de Liao
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Abstract
A series of conjugated polymer-based nanoparticles having far-red/near infrared emission ranges are disclosed. Cross coupling methods to prepare the conjugated polymers and methods of nanoparticle preparation are also discussed. The conjugated polymer nanoparticles are used as FR/NIR fluorescent probes in in vitro and in vivo biosensing and bioimaging applications, and are also used in photoacoustic imaging as contrast agents. Finally, use of the conjugated polymer nanoparticles in photothermal therapy is described.
Claims27
A conjugated polymer of formula (I):
- wherein:
- D is a conjugated system of one or more optionally substituted aromatic or heteroaromatic groups comprising:
- A1 is a conjugated system of one or more optionally substituted aromatic or heteroaromatic groups;
- A2 is a conjugated system of one or more optionally substituted aromatic or heteroaromatic groups;
- m is an integer from 1 to 100;
- n is an integer from 0 to 100;
- Y is C(R1)2, Si(R1)2, or NR1;
- Z is O, S or Se;
- each R1 is independently H, (CH2)pQ, (OCH2CH2)pQ
- p is an integer ranging from 1 to 24;
- R2 is (C1-C12)alkyl, (C6-C14)aryl, or (C1-C10)alkoxy(C1-C12)alkyl;
- Q is independently CH3, H, COOH, NH2, NH3+, N3, SH, SO3Na, PO3Na, or
- W is independently a fluorophore, a bioconjugate, a (C1-C100)alkyl group bound to a fluorophore or a bioconjugate, or a polyethyleneoxide group bound to a fluorophore or a bioconjugate;
- * is the point of attachment to A1, A2, or a polymeric unit;
- for n greater than or equal to 1, the energy band gap of A1 is larger than the energy band gap of A2;
- and
- further wherein the energy band gap of D is larger than the energy band gap of A1 and the energy band gap of A2.
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A conjugated molecule of formula (II):
- wherein:
- Ar1 is a polycyclic carbocyclic or heterocyclic aromatic group;
- Z is independently O, Se or S.
A method for making conjugated polymer-based nanoparticles, comprising:
- a) reacting an cross coupling partner of formula J-D-J;
- wherein D is
- J is independently B(OH)2, B(pin), B(cat), BF3K, B(O(CH2)3O) or Sn(C1-C4 (alkyl))3;
- Y is C(R1)2, Si(R1)2, or NR1;
- Z is O, S or Se;
- each R1 is independently H, (CH2)pQ, (OCH2CH2)pQ,
- p is an integer ranging from 1 to 24;
- R2 is (C1-C12)alkyl, (C6-C14)aryl, or (C1-C10)alkoxy(C1-C12)alkyl;
- Q is independently CH3, H, COOH, NH2, NH3+, N3, SH, SO3Na, or PO3Na;
- with a dihalide containing A1, and, for conjugated polymers of formula (I) for which n is not equal to zero, a second dihalide containing A2;
- A1 is a conjugated system of one or more optionally substituted aromatic or heteroaromatic groups;
- A2 is a conjugated system of one or more optionally substituted aromatic or heteroaromatic groups;
- in the presence of a palladium (0), palladium (II), nickel (0) or nickel (II) catalyst;
- to produce a conjugated polymer of formula (I)
- m is an integer from 1 to 100;
- n is an integer from 0 to 100;
- b) adding the conjugated polymer of formula (I) from step a) that is solubilized or suspended in at least one organic solvent into aqueous solution, enabling the self-assembly of the conjugated polymers into nanoparticles.
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Dependencies are inferred from the claim text.