Molecular Recognition of Spermine using Aggregation‐Induced Emission

Abstract

In this communication we report the synthesis and characterisation of a novel dianionic compound with aggregation‐induced emission properties. This compound was able to recognize spermine via a multivalent electrostatic interaction leading to a restriction of intramolecular rotation enhancing the fluorescence emission. This recognition was investigated in detail using UV‐Vis and fluorescence spectroscopy. Furthermore the binding stoichiometry was determined via isothermal titration calorimetry. Besides that the structure of the compound was confirmed by X‐ray crystallography. To proof the bivalent binding a singly negatively charged control compound was synthesized showing no specific interaction with the amines screened. Theoretical calculations were performed to get a deeper insight in the molecular structure and the electronic transitions.

Take your Positions and Shine: Effects of Positioning Aggregation‐Induced Emission Luminophores within Sequence‐Defined Macromolecules

“…This can then be detected and correlated to the binding event. Such AIE sensors have been developed towards the recognition of chemicals compounds such as explosives [9] or vapors [10] and bioamines [11] . Furthermore, they can be applied as biosensors for the detection of amino acids and proteins or for monitoring conformational changes of DNA or proteins [4,12] as well as bioimaging [13] .…”

“…Such AIE sensors have been developed towards the recognition of chemicals compounds such as explosives [9] or vapors [10] and bioamines. [11] Furthermore, they can be applied as biosensors for the detection of amino acids and proteins or for monitoring conformational changes of DNA or proteins[ 4 , 12 ] as well as bioimaging. [13] Along those lines, AIEs can also serve as a biomarker for diagnosing diseases as recently demonstrated by Lou and Xia for a real‐time quantitative light detection of telomerase in the urine of bladder cancer patients with a cationic AIE tetraphenylethene derivative.…”

Understanding the Role of Chalcogens in Ether‐Based Luminophores with Aggregation‐Induced Fluorescence and Phosphorescence

“…One of first selenium containing phosphor was described by Bonifazi in 2015 . Here phosphorescence was observed in a glassy matrix at 77 K. Recently, our group was able to synthesize a library of thioether‐based AIE luminophores which were used for different purposes, such as supramolecular assembly into organogels, micelles and nanorods, as well as their application in molecular recognition of small bioactive ligands . Within this library, two compounds were identified as phosphorescent units with excited state lifetimes reaching up to 5 μs and emission in the yellow‐orange region of the electromagnetic spectrum.…”

Understanding the Role of Chalcogens in Ether‐Based Luminophores with Aggregation‐Induced Fluorescence and Phosphorescence

“…[17] Here phosphorescence was observed in a glassy matrix at 77 K. Recently, our group was able to synthesize a library of thioether-based AIE luminophores [18] which were used for different purposes, such as supramolecular assembly into organogels, [19] micelles [20] and nanorods, [21] as well as their application in molecular recognition of small bioactive ligands. [22] Within this library, two compounds were identified as phosphorescent units with excited state lifetimes reaching up to 5 μs and emission in the yellow-orange region of the electromagnetic spectrum. Herein, we expanded our scope to a whole series of chalcogens including oxygen, sulphur, selenium and tellurium to understand the role of these heteroatoms on the emission wavelength, photoluminescence quantum yields and excited state lifetimes.…”