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This study was conducted to determine the relationship between dye structure, particularly the structural charge and flexibility, and binding affinity. We also investigated the effect of multivalency on the maximum fluorescence intensity by conjugating varying numbers of monovalent fluorochromes on nanoparticles. Fluorochrome-conjugated nanoparticles were synthesized by conjugating N-hydroxysuccinimide ester of quinolinium,4-[(3-methyl-2(3H)-benzothiazolylidene)methyl]- 1-[3-(trimethylammonio)propyl]-,iodide (TO-PRO 1 NHS ester) into aminated nanoparticles. The half maximum effective concentration (EC50) of DNA-binding fluorochromes and fluorochrome-conjugated nanoparticles for double- stranded nucleic acid (dsDNA) was investigated by fluorescence. Two important factors regulating the binding characteristics of fluorochromes were studied: the number of positive charges and the structural flexibility. Positive charge enhancement of binding affinity was observed in various systems. TO-PRO 1, which has two positive charges, showed higher binding affinity than TO. Rigid structured dyes, propidium iodide and 4?,6-diamidino-2-phenylindole (DAPI), exhibited significantly lower maximum fluorescence than TO-PRO 1, even though they both have two positive charges. The dye with three positive charges, SYTOX Green, showed higher binding affinity than TO-PRO 1. TO-PRO 1 dimer (TO-TO), which has four positive charges, showed the highest binding affinity to DNA. Flexible dyes exhibited more than 1000-fold higher fluorescence upon binding to dsDNA. The multivalency of the fluorochromes on the nanoparticles revealed that a shorter distance between fluorochromes was related to higher maximum fluorescence intensity. The fluorescence intensity of multivalent fluorochromes was substantially dependent on the distance between the monovalent sites. [Figure not available: see fulltext.].

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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A method of synthesising a compound of formula I: comprising the step of reacting a moiety of formula II: with a moiety of formula III: in compressed carbon dioxide in the presence of a transition metal catalyst and a base, wherein L is a labile leaving group; RN1 is optionally substituted C5-20 aryl; RN2is selected from optionally substituted C5-20aryl, optionally substituted C3-20 heterocyclyl, optionally substituted C3-7 alkyl, and optionally substituted sulfonyl; RN3 is selected from H and optionally substituted C1-7 alkyl, C3-20 heterocyclyl and C5-20aryl; or RN2 and RN3 together with the nitrogen atom to which they are attached form optionally substituted nitrogen-containing C3-20heterocylyl or C5-20 heteroaryl; and R1 R2 and R3 are independently selected from optionally substituted C1-7alkyl, C5-20 aryl, C3-20 heterocyclyl, hydroxy, halo, amino and C1-7 alkoxy, or two of R1, R2 and R3, together with the silicon atom to which they are attached, may form a silicon containing C5-7 heterocyclyl group.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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A library of 1,2- cyclometalated Pt(II) complexes based on various bidentate N,C-chelate chromophores have been studied for their uses as luminescent oxygen sensing probes (OSPs). The bidentate chelate ligands have been found to have a distinct impact on the performance of the Pt(II) compounds as OSPs. For some of the complexes, attachment of a dimesityl boron group (BMes2) to the chelate ligands enhances their oxygen sensitivity. For phenyl-1,2,3-triazole (Phtrz) based Pt(II) complexes, the attachment of a diphenyl amino moiety to the N,C-chelate ligand substantially enhances phosphorescence quenching and the performance of the OSP. A high kSVapp value (0.0667 Torr?1) for the OSP based on the diphenyl amino functionalized Pt(II) complex was achieved, which is the highest value reported to date for OSPs based on bidentate Pt(II) complexes.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Oxazolidin-2-one was found to be a facile ligand for the N-arylation of pyrrole, indole, and imidazole with aryl and heteroaryl iodides, bromides, and chlorides by applying Cul as catalyst. The easy preparation, commercial availability, lower molecular weight, and broad substrate applicability, as well as substituent compatibility of this catalysis system render oxazolidin-2-one great advantages over the Cu-catalyzed methods that have already been utilized in a number of applications.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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The highly regioselective PtCl4-catalyzed reaction of indoles with beta-allenols in THF at room temperature afforded indole derivatives containing a six-membered ether ring at the 3-position in moderate isolated yields. On the basis of a D-labeling experiment, a mechanistic rationale was proposed.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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o- and/or p-naphthoquinone methides (NQMs) can be selectively prepared by the ring opening of 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene derivatives based on a substituent effect at the 4 position of the substrates. The 4-alkyl- or silyl-substituted 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene was transformed to o-NQM (1-naphthoquinone-2-methide), which underwent Friedel-Crafts 1,4-addition of the alpha,beta-unsaturated carbonyl moiety to provide the 2-benzyl-1-naphthol as the biarylmethane and [4 + 2]-cycloaddition with a dienophile to give the fused heterocyclic arene. Meanwhile, the 4-unsubstituted 1-(siloxymethyl)-1,4-epoxy-1,4-dihydronaphthalene could be converted to the corresponding 4-benzyl-1-naphthol by the Friedel-Crafts 1,6-addition of p-NQM (1-naphthoquinone-4-methide) generated by the site-selective ring opening of the 1,4-epoxy moiety. Furthermore, the 4-(siloxymethyl)-(1,4-bis(siloxymethyl))-1,4-epoxy-1,4-dihydronaphthalene was transformed into a 2,4-bisbenzyl-1-naphthol or pentacyclic derivative via both the o- and p-NQM intermediates.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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An efficient method for intermolecular hydroarylation of aryl and aliphatic alkenes with indoles using a combination of [(PR3)AuCl]/AgOTf as catalyst under thermal and microwave-assisted conditions has been developed. The gold(I)-catalyzed reactions of indoles with aryl alkenes were achieved in toluene at 85C over a reaction time of 1-3 h with 2 mol% of [(PR 3)AuCl]/ AgOTf as catalyst. This method works for a variety of styrenes bearing electron-deficient, electron-rich, and sterically bulky substituents to give the corresponding products in good to high yields (60-95%). Under microwave irradiation, coupling of unactivated aliphatic alkenes with indoles gave the corresponding adducts in up to 90% yield. Selective hydroarylation of terminal C=C bond of conjugated dienes with indoles gave good product yields (62-81 %). On the basis of deuteriumlabeling experiments, a reaction mechanism involving nucleophilic attack of Au(I)-coordinated alkenes by indoles is proposed.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Acridine and carbazole derived electron donors, 8,8-dimethyl-5-phenyl-8,13-dihydro-5H-indolo[2,3-c]acridine (4IA) and 13,13-dimethyl-11-phenyl-11,13-dihydro-5H-indole[2,3-b]acridine(3IA), were synthesized as strong donor moieties of thermally activated delayed fluorescent (TADF) emitters. The new donor moiety was included in the molecular structure of diphenyltriazine based TADF emitter to study the effect of geometrical structure of the donor on the photophysical and device characteristics of TADF emitters. The 4IA donor was better than the 3IA donor for small singlet-triplet energy splitting and TADF emission. TADF behavior was observed only in the 4IA based TADF emitter due to geometrical structure. A TADF emitter having the 4IA based donor moiety exhibited a blue color coordinate of (0.21, 0.31) and a quantum efficiency of 13.7%.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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An efficient iron-promoted alkylation of indoles with enamides has been accomplished under mild reaction conditions. The reaction proceeded with remarkable regioselectivity leading exclusively to substitution by indoles at alpha-position of enamides.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Air- and moisture-stable and recyclable palladium nanoparticles supported on modified single-walled carbon nanotubes (SWCNT-Met/Pd) behave as very efficient heterogeneous catalysts in the Ullmann coupling of imidazoles and indoles with aryl iodides to afford the corresponding C-N coupling reactions under aerobic conditions. These cross coupled products were produced in excellent yields at low palladium loading (?0.2 mol%) and the heterogeneous catalyst can be readily recovered by simple filtration and reused five times without a noticeable loss in its catalytic activity.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles