An unexpected dual-emissive luminogen with tunable aggregation-induced emission and enhanced chiroptical property

Abstract

In the literature, organic materials with both aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ) effects that can emit with multiple bands both in the solution and aggregated state are rarely reported. Herein we report a novel chiral dual-emissive bismacrocycle with tunable aggregation-induced emission colors. A facile four-step synthesis strategy is developed to construct this rigid bismacrocycle, (1,4)[8]cycloparaphenylenophane (SCPP[8]), which possesses a 1,2,4,5-tetraphenylbenzene core locked by two intersecting polyphenylene-based macrocycles. The luminescent behavior of SCPP[8] shows the unique characteristics of both ACQ effect and AIE effect, inducing remarkable redshift emission with near white-light emission. SCPP[8] is configurationally stable and possesses a novel shape-persistent bismacrocycle scaffold with a high strain energy. In addition, SCPP[8] displays enhanced circularly polarized luminescence properties due to AIE effect.

Expanding new chemistry of aza-boracyclophanes with unique dipolar structures, AIE and redox-active open-shell characteristics

“…S20b†) is the consequence of structural functionalization with tetraphenylethyl (TPE) groups. 10,12 To the best of our knowledge, tricoordinated organoboranes including boron-based macrocycles have rarely been reported to show AIE properties. 13 Our molecular design for the optically reversed emission transition from ACQ to AIE represented by MC-BN5 and MC-ABN5 affords a new approach to aggregated macrocyclic chemistry, and it may also provide a proof of concept for supramolecular assembly using polar-structured π-conjugated cyclics.…”

“…More importantly, peripheral substitutions of tetraphenylethyl (TPE) units at the π-ring structure of MC-ABN5 with radial p orbitals induced a transformation of aggregation-caused quenching (ACQ) to a rarely observed aggregation-induced emission (AIE) for π-conjugated macrocycles. 4 b ,6 n ,10 Our strategy may provide a new possibility to develop directions in supramolecular chemistry using highly stable dipolar macrocycles.…”

Hydrophobicity Directed Chiral Self‐Assembly and Aggregation‐Induced Emission: Diacetylene‐Cored Pseudopeptide Chiral Dopants

“…A high value of β=20.57 μm −1 (Figure S49) is obtained for F‐DA . These dialkynes may find applications in solar cell concentrators, bioprobes, chemosensor and imaging techniques [23, 30] . The addition of non‐chiral Aib‐based dialkynes ( B‐DA ) showed no effect on the textural features of 5CB .…”

Intramolecular Through-Space Interactions Induced Emission of Pillar[4]arene[1]dicyanobenzene

“…A feasible tactic to realize this purpose is to introduce macrocyclic blocks as bulky spatial spacers between two π-conjugated segments . More recently, functionalized macrocycles and their supramolecular assemblies emerged as light-emitting materials continue to underpin progress in areas such as two-photon excited emission, chiral luminescence, and single-molecule white-light emission, as evidenced by fluorescent systems involved with pillararenes, a new family of supramolecular macrocycle discovered by Ogoshi et al in 2008. , Note that the symmetrical and rigid pillar architectures and the remarkable host–guest properties make pillararenes satisfactory spatial spacers in regulating the arrangement of emissive fluorophores through bonds or noncovalent interactions. In addition, pillararenes represent a new class of aggregation-induced emission (AIE) fluorophores, which are highly emissive in their aggregated state but nonluminous in solution .…”