Synthesis of 4-Nitro-N-phenyl-1,8-naphthalimide Annulated to Thia- and Azacrown Ether Moieties

Abstract

Two convenient procedures for the synthesis of thia-and azacrown ether containing 4-nitro-1,8-naphthalimides have been developed. The first procedure is based on the amination of 1,8-naphthalic anhydride with crown-containing anilines. The second procedure includes the macrocyclization reaction of N-[1,2-bis(2-haloethoxy)phenyl]naphthalimide derivative with terminal thiols or methylamines. A strategy based on a macrocyclization is flexible and variable and also allows the use of the synthetic approach for more complex compounds.

Synthesis and applications of fluorescent-tagged scale inhibitors in water treatment. A review

“…A significant number of papers are devoted to the usage of naphthalic acid imide derivatives as fluorescent markers [59][60][61][62][63]. This class of compounds has already found a wide range of practical applications as fluorescent markers in biochemical analysis or sensors [59,60].…”

“…This class of compounds has already found a wide range of practical applications as fluorescent markers in biochemical analysis or sensors [59,60]. This is due to both the synthetic availability of 1,8-naphthalimide derivatives [61], including derivatives containing polymerized functional groups [62,63], and their outstanding optical characteristics (intensive absorption, high fluorescence quantum yields, high photostability, sensitivity of photophysical characteristics to the external media and the chemical nature of the introduced substituents). A noticeable advantage of the optical platform of 1,8-naphthalimide is the possibility of adjusting the optical properties by varying substituents in the 4th position of the naphthalimide nucleus.…”

Fluorescent Markers in Water Treatment

“…Several publications report on the naphthalic acid-based markers for biochemical analysis application [60,61]. An interest in these reagents is associated with both synthetic availability of some valuable 1,8-naphthalimide derivatives and with promising optical properties [62][63][64]. Ecolab Inc. (USA) has proposed fluorescent monomers derived from 3,4-7H-benzo [d,e] anthracenedicarboxylic acid for the antiscalant labeling [65].…”

Graphocrown—A Novel, Two-Dimensional Oxocarbon: A Theoretical Study

“…Inspired by graphether, as well as the coordination properties of crown ethers [30,31], in particular integrated into the graphene flaxes [32,33], we decided to combine these concepts and developed a covalent organic framework (COF) that would consist of grapheneplanar crown ethers-the graphocrown. One of the key features of the new material is its preorganisation and fixed pore size.…”