Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8‐Naphthalimide Derivatives Containing Different Chromophores

Abstract

A series of 1,8-naphthalimide-based fluorophores containing different chromophores with varying conjugation and electron richness at the imidic nitrogen atom are synthesized and characterized. These amine-functionalized naphthalimides are bipolar in nature and exhibit interesting optical and morphological variations attributable to the nature of the N substituents. Despite the fact that the dyes are structurally different owing to variation of the substituent on the imidic nitrogen atom, their electronic characteristics are similar and originate from the 4-aminonaphthalimide segment. Nevertheless, they exhibit variations in morphology in the microscopic domain, and this is attributable to structural differences. Further, these fluorescent dyes display biocompatibility and are used in the bioimaging of cells.

Metal–Organic Framework with Color-Switching and Strongly Polarized Emission

“…Organic chromophores are widely used for biological imaging, , biorecognition, sensing, , and laser applications . These functions generally require a chromophore with good photostability and high fluorescence quantum yield.…”

A systematic review on 1,8-naphthalimide derivatives as emissive materials in organic light-emitting diodes

“…Since the OLED working is based on the holeelectron recombination in the EML, the color emitted by a NI-based device depends primarily on the electronic features of the material [4,[80][81][82][83]. Moreover, the variations in the chemical, photophysical and excited-state optical behavior of NIs are extremely sensitive to the nature and position of the substituents in the aromatic system [66,[84][85][86]. Thus, NI derivatives with desired features can be synthesized by the reaction of suitable amines with appropriate 1,8-naphthalic anhydrides, which enable to achieve various functionalized derivatives of imide nitrogen and substituted NI skeleton.…”

Tunable Self-Assembly and Aggregation-Induced Emission Characteristics of Triarylboron-Decorated Naphthalimides

“…Tuning the optical properties of fully carbon based conjugated systems by integrating boron into them is an attractive stratagem to develop materials with advanced properties and applications such as nonlinear optics, light-emitting devices, sensors, bioimaging, and external stimuli-responsive materials. , Recently, we became interested in developing boron-based multiple emissive molecular systems . During the course of our study we have established that tweaking the molecular conformation by judiciously perturbing the electronic structure of luminophores has a significant effect on their optical properties. , Having studied optical and structural features of TAB − and NPI − individually, we set out to investigate the optical and morphological characteristics of TAB-NPI conjugates. We envisioned that, by carefully balancing the intermolecular interactions via controlling the steric and electronic factors between intrinsically propeller TAB and planar NPI moieties, one can develop luminescent materials with tunable morphologies.…”

“…Of various organic molecular materials, 1,8-naphthalimides (NPIs) have received considerable attention in recent times owing to their potential applications in molecular sensors, optoelectronic materials, DNA intercalators, anticancer agents, , and live cell imaging . Despite their great advantages, the solid-state luminescence quantum efficiencies of NPI derivatives are very low due to aggregation-caused quenching (ACQ), caused by intermolecular face-to-face π–π interactions .…”