Quinoxaline-Bridged Porphyrinoids

Abstract

Quinoxaline-bridged porphyrinoids (3), the first macrocycles containing dipyrrolylquinoxaline (DPQ, 1) subunits, were synthesized from the condensation of the diformyl-substituted DPQ derivatives (2) and 1,8-diaminoanthracene. The resulting structures were confirmed by X-ray analyses, which showed encapsulation of CHCl(3) molecules within the columnar channels established by the stacked arrangement of the individual macrocycles. The solution phase interactions with fluoride and dihydrogenphosphate anions were studied in the case of the unsubstituted system 3a in CH(2)Cl(2). The binding affinities for these anions, studied at the tetrabutylammonium salts, were found to be enhanced relative to those of the simple, unsubstituted monomeric DPQ "parent" system (1a), presumably as the result of the combined effects of preorganization and cooperative binding permitted by the pyrrole NH donor groups. Positive homotropic allosteric anion binding was observed and is ascribed to the structurally coupled nature of the two binding cavities present in the macrocycles. Support for this latter contention came from energy minimization studies.

Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts

“…Quinoxaline moieties, have also found applications as dyes [23], cavitands [24], efficient electroluminescent materials [25], building blocks in the synthesis of organic semiconductors [26], chemically controllable switches [27] and dehydroannulenes [28].…”

Synthesis, Electrochemical and Mass Spectrometric Properties of the Macrocycles with One, Two and Four 3,3´-Biindolizine Redox-Active Fragments on the 3-(Indolizin-2-yl)quinoxalin-2-one Platform

“…[7] Основным же подходом явля-ется пошаговый синтез. [2,8,9] Известны примеры синтеза макроциклических олигоанилинов, [5,7] олигопириди-нов, [1,8] олигопирролов, [10][11][12] олиготиофенов, [2,4,5] олиго-карбазолов. [3] Олигохиноксалиновые или олигоиндоли-зиновые макроциклы не получены.…”

An Efficient and Recyclable Nanoparticle-Supported Cobalt Catalyst for Quinoxaline Synthesis

“…Examples of quinoxalinecontaining pharmacological entities are shown in Figure 1. In addition, quinoxalines have been applied as building blocks for the development of macrocyclic molecular receptors [12,13], semiconducting materials [14][15][16][17][18][19][20], dyes [21], cavitands [22] and luminescent materials [23]. Generally, quinoxalines can be prepared via a double condensation of 1,2-phenylenediamines with 1,2-diketones [24][25][26][27][28].…”