807610-46-4

Upstream product

• 17135-74-9 1,8-dibromonaphthalene 
• 783325-79-1 3-(3',5'-dimethylphenyl)-9-trimethylstannylacridine 
• 783325-77-9 9-bromo-3-(3',5'-dimethylphenyl)acridine 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 59748-90-2 4-Bromo-2-chloro-benzoic Acid 
• 884323-18-6 4-(3',5'-dimethylphenyl)-2-(N-phenylamino)benzoic acid 
• 884323-17-5 4-(3',5'-dimethylphenyl)-2-chlorobenzoic acid 

Relevant academic research and scientific papers

Synthesis of a sterically crowded atropisomeric 1,8-diacridylnaphthalene for dual-mode enantioselective fluorosensing

An efficient synthetic route to a sterically crowded 1,8- diheteroarylnaphthalene-derived enantioselective fluorosensor that operates in two different detection modes utilizing fluorescence lifetime and intensity has been developed. Screening of palladium-catalyzed Negishi, Kumada, Suzuki, Hiyama, and Stille coupling methods showed that the latter affords highly congested 1,8-diarylnaphthalenes in superior yields. Despite severe steric hindrance, axially chiral 1,8-bis(3-(3′,5′-dimethylphenyl)-9- acridyl)naphthalene, 1, was obtained in 68% yield from 1,8-dibromonaphthalene, 14, and 3-(3′,5′-dimethylphenyl)-9-tributyl-stannylacridine, 13, via two consecutive Stille cross-coupling steps using tetrakis(triphenylphosphine)- palladium(0) as catalyst in the presence of copper(II) oxide. The preparation of 1 involved formation of 4-(3′,5′-dimethylphenyl)-2-chlorobenzoic acid, 7, through microwave-assisted Suzuki coupling of 4-bromo-2-chlorobenzoic acid, 10, and 3,5-dimethylphenylboronic acid, 11, followed by regioselective amination with aniline and acridine ring construction in phosphorus oxybromide. Lithiation, subsequent treatment with trimethylstannyl chloride, and Stille cross-coupling then completed the five-reaction sequence providing 1 in 57% overall yield. The enantiomers of 1 were separated by semipreparative HPLC on a (R,R)-Whelk-O 1 column and successfully employed in enantioselective fluorosensing of N-t-Boc-protected serine, 20, glutamine, 22, proline, 23, and 2-hydoxy-2-methylsuccinic acid, 21. Fluorescence titration experiments with 23 revealed that both static and dynamic quenching occur with distinctive enantioselectivity. Addition of (R)-23 to a solution of (+)-1 in acetonitrile resulted in stronger fluorescence quenching than titration with the (S)-enantiomer of 23. The fluorescence lifetime, τ, of 1 was determined as 18.8 ns and steadily decreased to 7.5 and 6.8 ns in the presence of 0.1 M of (S)-23 and (R)-23, respectively.

Stereoselective UV sensing of 1,2-diaminocyclohexane isomers based on ligand displacement with a diacridylnaphthalene N,N′ -dioxide scandium complex

Stereoselective displacement of diacridylnaphthalene N,N′-dioxide ligands, 1, from a scandium(III) complex can be used for quantitative detection of 1,2-diaminocyclohexane isomers. The diastereoselective sensing assay with Sc(syn-1)2 shows exce

Determination of enantiomeric excess and concentration of chiral compounds using a 1,8-diheteroarylnaphthalene-derived fluorosensor

Enantioselective fluorosensing using a rigid C2-symmetric 1,8-diacridylnaphthalene N,N′-dioxide sensor allows accurate determination of both the enantiomeric composition and concentration of several analytes capable of chiral hydrogen bonding.

Determination of enantiomeric excess and concentration of unprotected amino acids, amines, amino alcohols, and carboxylic acids by competitive binding assays with a chiral scandium complex

A practical UV-vis sensing method for enantioselective microanalysis of unprotected amino acids, amines, amino alcohols, and carboxylic acids in aqueous solution has been developed. Both concentration and enantiomeric composition of a wide range of chiral

Enantioselective sensing of chiral carboxylic acids

A chiral 1,8-diacridylnaphthalene-derived fluorosensor has been prepared and used for enantioselective sensing of a broad variety of chiral carboxylic acids including amino acids, aliphatic acids, arylalkanoic acids, and halogenated carboxylic acids. Fluo