One-pot protocol for J-aggregated anthraimidazolediones catalyzed by phosphotungstic acid in PEG-400 under aerobic condition. Issue 26 (23rd February 2016)

• Record Type: Journal Article
• Authors: Bhattacharyya, Bhaswati; Kundu, Arijit; Das, Aniruddha; Dhara, Kaliprasanna; Guchhait, Nikhil
• Is Part Of: RSC advances. Volume 6:Issue 26(2016)
• Page Start: 21907
• Page End: 21916
• Publication Date: 2016-02-23
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5ra19190d
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : One-pot protocol for anthra[1, 2- d ]imidazole-6, 11-dione was developed via tandem cyclocondensation cum oxidation, catalyzed by phosphotungstic acid in PEG-400 support in open air. J-aggregation properties of products were confirmed by photophysical studies. Abstract : A precise and productive one pot green protocol has been developed for the chemoselective synthesis of anthra[1, 2- d ]imidazole-6, 11-diones using phosphotungstic acid (PTA) as a reusable catalyst on polyethylene glycol-400 (PEG-400) support under aerobic condition. It involves a simple synthetic procedure for a wide range of anthraimidazolediones from 1, 2-diaminoanthraquinone and various aldehydes possessing π-enriched aromatic/heteroaromatic rings and lipophilic alkyl chains. In inert atmosphere, the reaction followed a different pathway, yielding a unique naphtho-quinoxaline derivative. Synthesized anthraimidazoledione derivatives had shown different self-aggregation morphologies influenced by the substitution pattern. A nice agreement between crystal packing pattern and photophysical properties with J-aggregation morphology was also observed. Representative derivatives exhibited contrasting fluorescence behaviors in transition from solution state to nanostructured solid state.