Synthesis, Characterization, and Crystal Structures of Imides Condensed with p-Phenylamino(Phenyl) Amine and Fluorescence Property.

Jing Zhang,Huaibo Ma

doi:10.3390/ma12111873

Abstract

A series of aromatic diimide and monoimide compounds condensed with p-phenylamino(phenyl)amine were synthesized and confirmed by Proton Nuclear Magnetic Resonance (1H NMR), Carbon-13 Nuclear Magnetic Resonance (13C NMR), Fourier Transform Infrared Spectroscopy (FT-IR), Elemental Analysis (EA), and High Resolution Mass Spectroscopy (HRMS). Meanwhile, single crystal X-ray diffraction showed the existence of intermolecular N···O hydrogen bonds, which affected the thermal stabilities of corresponding compounds by the support of Thermalgravimetric Analysis (TGA) curves. The steady-state UV-vis absorption peaks of synthetic compounds 1–6 appeared in the range of 220–380 nm. Fluorescence emission spectra showed peaks in the range of 290–420 nm. Meanwhile, deep-blue or violet-blue emissions for 2, 4, and 5 in THF under excitations of 254 nm and 365 nm, respectively, were observed at room temperature in air. Furthermore, Differential pulse voltammetry (DPV) and cyclic voltammogram CV were conducted within −1.5–+1.5 V to show quasi-reversible behavior for conjugated compounds and irreversible behavior for less conjugated ones.

Highlights

Conjugated organic polymers and small molecules display both charge and energy transfer properties through π–π or π–n–π, which are affected by intrinsic structures, packing modes, and morphology [1,2,3]
Applications were found in organic nonvolatile memories (ONVMs) [4], organic field-effect transistors (OFETs) [5,6], single molecular switch [7], photonics [8], organic solar cells (OSCs) [9], organic rechargeable lithium-/sodium ion batteries [10,11,12,13], and electrochromism [14,15,16]
A few rylene diimides, such as perylene diimide dyes [23,24] and naphthalene diimide derivatives [25,26,27], showing fluorescence property in solid state were synthesized with non-arylamine, regardless of the aggregation-caused quenching (ACQ) effect, leading to weak or quenched fluorescence property in solid state [28]

Summary

Introduction

Conjugated organic polymers and small molecules display both charge and energy transfer properties through π–π or π–n–π, which are affected by intrinsic structures, packing modes, and morphology [1,2,3]. Rylene diimides were widely studied, due to their high electron mobilities because of long range conjugation and high thermal and oxidative stabilities [17]. Multifunctional properties on rylene diimides were explored as molecular imaging agents [18,19] and probes [20,21,22]. To investigate the binding process for small molecules to DNA motivated by discovering drugs, fluorescence property on both naphthalimide-based Schiff base derivatives, reported by Uddin [29], and A few rylene diimides, such as perylene diimide dyes [23,24] and naphthalene diimide derivatives [25,26,27], showing fluorescence property in solid state were synthesized with non-arylamine, regardless of the aggregation-caused quenching (ACQ) effect, leading to weak or quenched fluorescence property in solid state [28].

Methods

Results

Conclusion