The subject invention pertains to compositions of a probe comprising two pH-reversible forms, including the boron dipyrromethene (BODIPY) fluorescent form and the non-fluorescent leuco-BODIPY form, for use in confocal imaging methods of intracellular vesicles as well as extracellular vesicles that are present in conditioned culture medium and/or secreted by living cells, without inducing severe cytotoxicity.

The subject invention pertains to compositions of a probe comprising two pH-reversible forms, including the boron dipyrromethene (BODIPY) fluorescent form and the non-fluorescent leuco-BODIPY form, for use in confocal imaging methods of intracellular vesicles as well as extracellular vesicles that are present in conditioned culture medium and/or secreted by living cells, without inducing severe cytotoxicity.

A fluorescent material and a method of synthesizing thereof are provided. The fluorescent material includes a formula (1) as follows:

##STR00001##

formula (1), and Y is N or B; X.sub.1 and X.sub.2 are the same or different; X.sub.1 and X.sub.2 are selected from C or Si; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different; R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are selected from a hydrogen atom, an alkyl group, an aromatic hydrocarbon group, or a heteroaryl group; R.sub.5, R.sub.6, R.sub.7, and R.sub.8 are the same or different; R.sub.5, R.sub.6, R.sub.7, and R.sub.8 are selected from an alkyl group, an aromatic hydrocarbon group, or a heteroaryl group; or R.sub.5 and R.sub.6 form a cyclic group; or R.sub.7 and Rs form a cyclic group.

A compound, a photosensitive resin composition including the same, a color filter manufactured using the photosensitive resin composition, and a CMOS image sensor including the color filter, the compound being represented by Chemical Formula 1:

A-L-B.  [Chemical Formula 1]

A rapid and facile design strategy to create a highly complex optical tag with programmable, multimodal photoluminescent properties is described. This is achieved via intrinsic and biomolecule-fluorophore hidden signatures. As a first covert feature of the tag, an intricate novel heterometallic near-infrared (NIR) emitting mesoporous metal-organic framework (MOF) was synthesized comprising homometallic hexanuclear clusters based on Nd and Yb. To generate controlled, multimodal, and tailorable emission with difficult to counterfeit features, the NIR emissive MOF was post-synthetically modified via a fluorescent biomolecule labeling design strategy. The surface attachment of several distinct fluorophores, including the simultaneous attachment of up to three distinct fluorescently labeled DNA oligos was demonstrated, with excitation and emission properties across the visible spectrum (480-800 nm). The DNA inclusion as a secondary covert element in the tag was demonstrated via detection of SYBR Gold dye association.

A rapid and facile design strategy to create a highly complex optical tag with programmable, multimodal photoluminescent properties is described. This is achieved via intrinsic and biomolecule-fluorophore hidden signatures. As a first covert feature of the tag, an intricate novel heterometallic near-infrared (NIR) emitting mesoporous metal-organic framework (MOF) was synthesized comprising homometallic hexanuclear clusters based on Nd and Yb. To generate controlled, multimodal, and tailorable emission with difficult to counterfeit features, the NIR emissive MOF was post-synthetically modified via a fluorescent biomolecule labeling design strategy. The surface attachment of several distinct fluorophores, including the simultaneous attachment of up to three distinct fluorescently labeled DNA oligos was demonstrated, with excitation and emission properties across the visible spectrum (480-800 nm). The DNA inclusion as a secondary covert element in the tag was demonstrated via detection of SYBR Gold dye association.

The present disclosure provides a non-peripheral quaternary ammonium-modified zinc phthalocyanine and a preparation method and use thereof, belonging to the field of preparation of photodynamic drugs or photosensitizers. The non-peripheral quaternary ammonium-modified zinc phthalocyanine can be used as a photosensitizer for a photodynamic therapy (PDT) and photodynamic diagnosis, and can also be used for a photodynamic-immune synergistic therapy. Due to a unique structure, the non-peripheral quaternary ammonium-modified zinc phthalocyanine can be combined with an immune checkpoint blocker to achieve an excellent synergistic anti-tumor effect, which has a significant prospect for use in treating a metastatic tumor.

Use of transition metal complexes of the formula (I) in organic light-emitting diodes

##STR00001## where: M.sup.1 is a metal atom; carbene is a carbene ligand; L is a monoanionic or dianionic ligand; K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a π complex with M.sup.1; n is the number of carbene ligands and is at least 1; m is the number of ligands L, where m can be 0 or ≥1; is the number of ligands K, where o can be 0 or ≥1; where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also
an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific transition metal complexes comprising at least two carbene ligands.

Use of transition metal complexes of the formula (I) in organic light-emitting diodes

##STR00001## where: M.sup.1 is a metal atom; carbene is a carbene ligand; L is a monoanionic or dianionic ligand; K is an uncharged monodentate or bidentate ligand selected from the group consisting of phosphines; CO; pyridines; nitriles and conjugated dienes which form a π complex with M.sup.1; n is the number of carbene ligands and is at least 1; m is the number of ligands L, where m can be 0 or ≥1; is the number of ligands K, where o can be 0 or ≥1; where the sum n+m+o is dependent on the oxidation state and coordination number of the metal atom and on the denticity of the ligands carbene, L and K and also on the charge on the ligands carbene and L, with the proviso that n is at least 1, and also
an OLED comprising these transition metal complexes, a light-emitting layer comprising these transition metal complexes, OLEDs comprising this light-emitting layer, devices comprising an OLED according to the present invention, and specific transition metal complexes comprising at least two carbene ligands.

The invention relates to novel fluorescent rhodamine dyes with enhanced cell permeability which are rhodamine 4′-isomers having the following general structural formula A: wherein Z is selected from O(alkyl), O(aryl), S(aryl), S(O)(alkyl), S(O) (aryl), S(O).sub.2(alkyl), S(O).sub.2(aryl), S(O).sub.2(—O-alkyl), S(O).sub.2(—O-aryl), S(O).sub.2NH(alkyl), S(O).sub.2NH(aryl), S(O).sub.2N(alkyl).sub.2, S(O).sub.2N(aryl).sub.2, S(O).sub.2N(alkyl)(aryl), C(O)O(alkyl), C(O)O(aryl), C(O)(alkyl), C(O)(aryl), P(O)OH(—NH-alkyl), P(O)OH(—O-alkyl), P(O)OH(—NH-aryl), P(O)OH(—O-aryl), P(O)(—O-alkyl).sub.2, P(O)(—NH-alkyl).sub.2, P(O)OH(—N(alkyl).sub.2), P(O)OH(—N(aryl).sub.2), P(O)(—N(aryl).sub.2).sub.2, P(O) (—N(alkyl).sub.2)(—N(alkyl).sub.2), P(O)(—O-aryl).sub.2, P(O)(—NH-aryl).sub.2, P(O)(—O-alkyl)(-O-aryl), P(O)(—NH-alkyl)(-O-aryl), P(O)(-O-alkyl)(-NH-aryl), P(O)(—NH-alkyl)(-NH-aryl), C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, in particular C(O)OH, C(O)NH(alkyl), C(O)NH(aryl), CON(alkyl).sub.2, CON(aryl).sub.2, C(O)O(alkyl) and C(O)O(aryl), or any group which is neither Cl, NH.sub.2 or NO.sub.2 and which induces a neighboring group effect via steric, ionic or bonding interactions with the adjacent carboxyl group resulting in a shift of the equilibrium between zwitterionic form and spirolactone form towards the spirolactone form. The invention further relates to 4′-isomer derivatives and probes comprising such 4′-isomers coupled to at least one reactive group or ligand which is capable to interact with or bind to other molecules, wherein said reactive group or ligand may be coupled to the rhodamine 4′-isomer fluorophore either directly or via a linker. Another aspect of the invention relates to the use of these compounds and conjugates as labels in microscopic, spectroscopic and other imaging techniques and/or as cell permeable substances penetrating through membranes of living and fixed cells in vivo or in vitro.

##STR00001##