Aggregation-induced emission, multiple chromisms and self-organization of N -substituted-1,8-naphthalimides
| Autor: | Yun Lu, Baoyan Li, Ben Dong, Xinlei Meng, Mei Yang, Han Yan, Shusheng Ge |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Quenching (fluorescence)
Process Chemistry and Technology General Chemical Engineering Stacking Quantum yield 02 engineering and technology Tetraphenylethylene 010402 general chemistry 021001 nanoscience & nanotechnology Triphenylamine Photochemistry 01 natural sciences 0104 chemical sciences Naphthalimides chemistry.chemical_compound Crystallography chemistry Phenyl group 0210 nano-technology Luminescence |
| Zdroj: | Dyes and Pigments. 148:147-153 |
| ISSN: | 0143-7208 |
| DOI: | 10.1016/j.dyepig.2017.08.013 |
| Popis: | Most aggregation-induced emission (AIE) luminogens possess propeller-like aromatic stator-rotor structures, such as silole, tetraphenylethylene (TPE) and triphenylamine (TPA), to restrict intra-molecular motions (RIM) and avoid aggregation-caused quenching (ACQ) effects. In our work, two simple N -substituted naphthalimides were designed and synthesized by the amide condensation to create novel AIE systems. Except for the same aromatic stator (naphthalimide), N -phenyl-1,8-naphthalimide ( PhNI ) contained an aromatic rotor (phenyl group) while N -cyclohexyl-1,8-naphthalimide ( CyNI ) contained an aliphatic rotor (cyclohexyl group). The PhNI samples obtained from different preparation processes showed multiple chromisms (MC) effects and varied levels of luminescence. Despite of the same intra-molecular structure, the crystal of PhNI had staggered parallel inter-molecular conformation with weak emission but the precipitation of PhNI had cross one with strong emission. Although without MC effects, CyNI gave an excellent fluorescence quantum yield (Φ f = 0.55). The experimental results and theoretical analyses suggested that the AIE effects were decided by intra- and inter-molecular structure simultaneously and the construction and destruction of inter-molecular π-π stacking between aromatic rotors in PhNI resulted in the MC effects. |
| Databáze: | OpenAIRE |
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