A fluorene-based material containing triple azacrown ether groups: synthesis, characterization and application in chemosensors and electroluminescent devices

Abstract

We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe(3+) but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe(3+), with the Stern-Volmer coefficients (Ksv) being 1.59 × 10(5) M(-1) in a solvent mixture of tetrahydrofuran and water (THF-H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe(3+) in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be -5.88 eV and -2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11 630 cd m(-2) and 1.47 cd A(-1), respectively, from 230 cd m(-2) and 0.03 cd A(-1) of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe(3+) and as an effective electron injection layer to enhance the performance of MEH-PPV.

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al3+, HF2–, and Nitro Explosives

“…In recent times, the design of sensors (ions or small molecules) and their application in live cells for the detection of ions/molecules have received active interest from chemistry, physics, chemical engineering, electrical and electronic engineering, and many other branches. On considering the social and biological importance of Al­(III), some examples of fluorescent sensors have been reported for Al 3+ detection with the Schiff base scaffold of 4-aminoantipyrine derivatives, rhodamine B ligands, coumarinyl derivatives, benzophenone, chromone, diphenyl pyrrol derivatives, pyrazoles, quinolones, fluorenes, benzimidazoles, and so forth. Besides, a limited number of sensors exhibit aggregation-induced emission (AIE), and their emissivity, in some cases, has been influenced by Al 3+ ions .…”

Nanostructuring with Surfactants: The Self-Assembly of a New Poly(thiophene-phenylene) Conjugated Polymer Bearing Azacrown Ether Pendant Groups

“…22,24−27 A multifunctional fluorene-based material containing triple azacrown ether, 2,4,7-tri[4-(monoaza-15-crown-5)styryl]-9,9-dihexylfluorene, was synthesized and successfully used as a chemosensor toward Fe 3+ , and also to enhance the electroluminescence of polymer light-emitting diodes (PLEDs) using an environmentally stable aluminum cathode. 20 Multilayer PLEDs were constructed with an electron injection layer (EIL) based on a water/alcohol soluble copoly(p-phenylene) with pendant azacrown ether and ethylene glycol ether groups doped with metal carbonate. 21 The device exhibit improved electron injection which resulted in significant enhancement of its performance.…”

“…The use of CP with pendant crown ether groups shows great potential and opens new technological possibilities since they combine the optoelectronic properties of CP and the sensitivity/selectivity of the crown ether moieties. This approach has been successfully demonstrated for a wide range of applications, such as chemical − and biological , sensors, polymer light-emitting diodes, − thermoresponsive materials for supramolecular gels, and bulk-heterojunction polymer solar cells . The dynamic and reversible properties of CPs make them suitable to monitor minor changes in the system and can be easily followed by optical methods, such as photoinduced electron transfer (PET), aggregation induced emission (AIE), and aggregation caused quenching (ACQ). ,− A multifunctional fluorene-based material containing triple azacrown ether, 2,4,7-tri­[4-(monoaza-15-crown-5)­styryl]-9,9-dihexylfluorene, was synthesized and successfully used as a chemosensor toward Fe 3+ , and also to enhance the electroluminescence of polymer light-emitting diodes (PLEDs) using an environmentally stable aluminum cathode .…”

Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9‐Diethylfluorene (Part I)

“…Fluorene‐based acyclic and macrocyclic molecules [1] as well as polymers [2] have been reported to have the potential for numerous applications ranging from organic transistors, solar cells and organic light‐emitting diodes to lasers. Compounds featuring a fluorene moiety have been further recognized as chemosensors for some cationic, [3a–c] anionic [3d] and neutral substrates [4] as well as agents for cell imaging [5] . In addition, fluorene derivatives have shown interesting biological activities, including antibacterial, [6a] antiviral, [6b] anticancer [7] and some others [8] .…”