Synthesis and Studies of the Properties of a Liquid-Crystalline Quaterrylenebis(dicarboximide) by ¹H NMR and UV−vis Spectroscopies

Abstract

The synthesis of an ionic quaterrylenebis(dicarboximide) 1a, a long-wavelength absorbing mesogen, is described. When compared with its analogue 2a, an ionic perylenebis(dicarboximide), the aromatic protons of 1a exchange with deuterium of concentrated D(2)SO(4) at a dramatically faster rate. In addition, stronger aggregation in aqueous media was observed for 1a.

Microwave-assisted Synthesis of Perylene-3,4-dicarboximides: Highly Photostable Fluorescent Dyes

“…The vessel was inserted into the microwave reactor (Discover, CEM Corp.) and irradiated at different temperatures, power settings, and for various time durations. Due to the poor solubility of some PDCIs, the reaction yield is determined from the isolation yield after the train sublimation (entry [4][5][6][8][9][10]. The reactions of substituted anilines or amines were studied next to determine their reactivities (Table I).…”

“…[9] Although the reaction yield is reasonable, between 45-62%, this procedure might not be suitable for some aryl substituted imides, owing to their poor solubility in acid and basic solutions. A typical synthesis of PDCIs required multiple synthetic steps and used perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) as the starting material.…”

Fused Polycyclic Aromatic Compounds with Near Infrared Absorption and Emission

“…Our next challenge was to find efficient approaches with the goal of accomplishing the ring-closure reaction. As a matter of fact, the last cyclization reaction was performed under different conditions such as (1) KOH in ethanol with glucose; 23 (2) t-BuOK/DBN in diglyme; 24 (3) FeCl 3 in nitromethane and dichloromethane; 25 and (4) K 2 CO 3 in ethanolamine. 26 It was found that the first three methods all failed and complicated mixtures were obtained probably due to the decomposition of NPDI units.…”

“…© Thieme Stuttgart • New YorkSynlett 2012,23,[171][172][173][174][175][176][177][178][179][180][181][182][183][184] …”

A Two-Step Synthesis of Quarterrylene Bisimides: Application of the ‘Green Route’ Method

“…However, this requires com-parably rough reaction conditions. Some improvements were obtained with the combination of KOH/glucose, 11,12 however, with varying results and a special treatment of the reaction products is required.…”