AIEE Active Donor–Acceptor–Donor-Based Hexaphenylbenzene Probe for Recognition of Aliphatic and Aromatic Amines

Abstract

In the present investigation, an intramolecular charge transfer (ICT) and aggregation induced emission enhancement (AIEE) active donor-acceptor-donor (D-A-D) system 5 having fumaronitrile as the acceptor and hexaphenylbenzene (HPB) as the donor moieties joined through rotatable phenyl rings has been designed and synthesized that is highly emissive in the solid state and exhibits stimuli-responsive reversible piezochromic behavior upon grinding and heating. Because of its AIEE characteristics, HPB derivative 5 undergoes aggregation to form fluorescent aggregates in mixed aqueous media that exhibit ratiometric fluorescence response toward aliphatic amines (primary/secondary/tertiary) and turn-off response toward aromatic amines and hence differentiates between them. Further, the solution-coated portable paper strips of derivative 5 showed pronounced and sensitive response toward aromatic and aliphatic amines with a detection limit in the range of picogram and nanogram level, respectively.

Through-space charge transfer hexaarylbenzene dendrimers with thermally activated delayed fluorescence and aggregation-induced emission for efficient solution-processed OLEDs

“…This conformation forces the aromatic units to face each other, enabling the through-space electron interactions between the aromatic rings in the periphery 29. By decorating the hexaphenylbenzene core with suitable donors and acceptors, HABs with redox chromophores have been constructed to show interesting properties and applications such as fluoride ion probing and organic amine recognition in recent years 26,30…”

‘Light‐Up’ AIE‐Active Materials: Self‐Assembly, Molecular Recognition and Catalytic Applications

“…The sensing events that took place between fluorescent assemblies and targeted analytes were based on different mechanisms such as aggregation‐deaggregation, electron/energy transfer and AIE‐TICT/AEE‐ICT phenomenon (Chart 1). We reported AEE‐ active donor‐acceptor‐donor system 2 for the detection and differentiation of aromatic and aliphatic amines [17] . Derivative 2 is synthesized by covalently linking AIE‐active HPB moieties to the fumaronitrile group.…”

Aggregation‐Induced Emission: A Tool for Sensitive Detection of Amines

“…In line with this, Kumar et al . developed aggregation‐induced emission enhancement (AIEE) active donor‐acceptor‐donor (D−A‐D) derivative 25 , where fumaronitrile act as an acceptor and hexaphenylbenzene (HPB) as the donor moieties for the detection of aliphatic and aromatic amines in solution as well as in vapor phase . The designed derivative 25 was highly emissive in the solid state and exhibits stimuli‐responsive reversible piezochromic behavior upon grinding and heating.…”