Preprint Article Version 1 This version is not peer-reviewed

Synthesis and Fluorescent Properties of Novel Mono- and Di-Substituted 1,8-Naphthalimide Derivatives at the C-4 Position

Version 1 : Received: 22 May 2017 / Approved: 23 May 2017 / Online: 23 May 2017 (08:10:02 CEST)

How to cite: Fu, Y.; Pang, X.; Wang, K.; Wang, Z.; Li, G.; Ye, F. Synthesis and Fluorescent Properties of Novel Mono- and Di-Substituted 1,8-Naphthalimide Derivatives at the C-4 Position. Preprints 2017, 2017050167 (doi: 10.20944/preprints201705.0167.v1). Fu, Y.; Pang, X.; Wang, K.; Wang, Z.; Li, G.; Ye, F. Synthesis and Fluorescent Properties of Novel Mono- and Di-Substituted 1,8-Naphthalimide Derivatives at the C-4 Position. Preprints 2017, 2017050167 (doi: 10.20944/preprints201705.0167.v1).

Abstract

A series of novel N-n-butyl-1,8-naphthalimide derivatives were synthesized via a three-step reaction involving nucleophilic substitution and acylation. All of the compounds were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis, and the crystal structure of N-n-butyl-4-[N’,N’-bis(2`,4`-dichlorobenzoyl)ethylamino]-1,8-naphthalimide was determined. The π-π stacking interactions and hydrogen bonds between the two molecular core planes (naphthalimide ring) and the van der Waals forces between the flexible n-butyl groups resulted in a 3D long-chain structure. The UV-vis and fluorescence properties of the title compounds were investigated. The results indicated that the monosubstituted 1,8-naphthalimide derivatives bearing an electron-donating group on the benzene ring or a structure with a larger conjugative effect exhibited enhanced fluorescence properties.

Subject Areas

N-n-Butyl-4-(N′,N′-dihydroxyethylamino)-1,8-naphthalimide; mono-substituted; di-substituted; synthesis, crystal structure; fluorescence

Readers' Comments and Ratings (0)

Leave a public comment
Send a private comment to the author(s)
Rate this article
Views 0
Downloads 0
Comments 0
Metrics 0
Leave a public comment

×
Alerts
Notify me about updates to this article or when a peer-reviewed version is published.