Tetraphenylethylene-embedded [1₅]paracyclophanes: AIEgen and macrocycle merged novel supramolecular hosts used for sensing Ni²⁺ ions

Abstract

Transformation of [15]paracyclophanes ([15]PCP) into fluorophores has been achieved by embedding a tetraphenylethene (TPE) unit into their skeletons at the meso position. The obtained two hosts demonstrated distinct aggregation-induced emission...

Pillar[5]arene Derivatives Embedded with Aggregation‐Induced Emission Luminogens and Their Fluorescence Regulation

“…In this structure, the dihedral angles between the benzene ring inside the macrocycle and the C=C bond plane are 65.26°and 64.21°, while the dihedral angles between the outer benzene ring and the C=C bond are 7.68°and 7.96°, which is almost close to a planar structure (Figure 1a). The dihedral angle between the slightly twisted [1 5 ]PCP plane and DPDBF plane is 17.96°(Figure 1b), which is slightly smaller than that of compound m-TPE mono-[1 5 ]PCP (27.1°) [15] we have reported. Intermolecular interactions are also critical for the fluorescence emission of the macrocycle.…”

“…[13] Recently, our group reported a novel macrocycle (m-TPE mono-[1 5 ]PCP), which was designed by incorporating tetraphenylethylene (TPE) AIEgens into the [1 5 ]PCP [14] scaffold at the meso-position. [15] Contrary to traditional modification of macrocycles on their rims, our methodology retains the integrity of macrocyclic scaffold. Meanwhile, the rotation of the propeller-like TPE unit is partially restricted, resulting in a distinct change in its fluorescent colour relative to free TPE.…”

“…Meanwhile, the intensity of fluorescence emission can be regulated by the specific host‐guest interaction of pillar[n]arenes with different guest molecules [13] . Recently, our group reported a novel macrocycle ( m ‐TPE mono‐[1 5 ]PCP ), which was designed by incorporating tetraphenylethylene ( TPE ) AIEgens into the [1 5 ]PCP [14] scaffold at the meso ‐position [15] . Contrary to traditional modification of macrocycles on their rims, our methodology retains the integrity of macrocyclic scaffold.…”

Pseudo[n]-pillar[5]arenes: Synthesis, Structures, and Host–Guest Binding Properties

“…Furthermore, Huang’s group reported the preparation of [1 5 ]­paracyclophenone and its fluorenone-containing derivatives by first oxidizing the methylene groups of [1 5 ]­PCP to carbonyl groups . Recently, tetraphenylene was incorporated into [1 5 ]­PCP skeleton at methylene-bridged sites via the McMurry coupling reaction. , However, the functionalization and partial derivatization of [1 n ]­PCP at phenylene sites have been rarely explored, and it remains a challenge to introduce different substituents to the phenyl rings of [1 n ]­PCP. Once this challenge is overcome, the diversity of the [1 n ]­PCP families will be greatly expanded and more properties of them will also be discovered.…”

Emissive Click Cages

“…The incorporation of multiple TPE or TBPE units into macrocycle or cage structure results in fewer conformational degrees of freedom and reduced intramolecular rotations. As a result, the resultant AIEgenic macrocycle and cage molecules exhibit emission even in dilute solutions, and further enhanced AIE [9–13] . The resulting system can be more sensitive to analytes.…”