783333-49-3

Basic information

• Product Name: anti-1,8-bis(3,3'-(3,5-dimethylphenyl)-9,9'-diacridyl)naphthalene
• CAS NO: 783333-49-3
• Molecular Weight: 690.887
• Mol File: 783333-49-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: anti-1,8-bis(3,3'-(3,5-dimethylphenyl)-9,9'-diacridyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: anti-1,8-bis(3,3'-(3,5-dimethylphenyl)-9,9'-diacridyl)naphthalene(783333-49-3)
• EPA Substance Registry System: anti-1,8-bis(3,3'-(3,5-dimethylphenyl)-9,9'-diacridyl)naphthalene(783333-49-3)

Safety Data

• Hazardous Substances Data: 783333-49-3(Hazardous Substances Data)

Upstream product

• 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 
• 17135-74-9 1,8-dibromonaphthalene 
• 783325-77-9 9-bromo-3-(3',5'-dimethylphenyl)acridine 
• 783325-79-1 3-(3',5'-dimethylphenyl)-9-trimethylstannylacridine 

Relevant articles and documents

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.

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.

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