Fluorescent and colorimetric ion probes based on conjugated oligopyrroles

Abstract

Metal ions and anions play important roles in many industrial and biochemical processes, and thus it is highly desired to detect them in the relevant systems. Small organic molecule based sensors for selective and sensitive detection of target ions show the advantages of low cost, high sensitivity and convenient implementation. In this area, pyrrole has incomparable advantages. It can be easily incorporated into linear and macrocyclic conjugated structures such as dipyrrins, porphyrins, and N-confused porphyrins, which may utilize the imino N and amino NH moieties for binding metal ions and anions, respectively. In this tutorial review, we focus on representative examples to describe the design, syntheses, sensing mechanisms, and applications of the conjugated oligopyrroles. These compounds could be used as colorimetric or fluorescent ion probes, with the advantages of vivid colour and fluorescence changes, easy structural modification and functionalization, and tunable emission wavelengths. Compared with normal porphyrins, simple di- and tripyrrins, as well as some porphyrinoids are more suitable for designing fluorescence "turn-on" metal probes, because they may exhibit flexible confirmations, and metal coordination will improve the rigidity, resulting in vivid fluorescence enhancement. It is noteworthy that the oligopyrrolic moieties may simultaneously act as the binding unit as well as the reporting moiety, which simplifies the design and syntheses of the probes.

An off-on fluorescent probe for specifically detecting cysteine and its application in bioimaging

“…In recent times, fluorescent molecular probes have emerged as an attractive tool for selective detection of various chemical and biological components [6][7][8][9][10], including thiols [11][12][13][14][15][16][17]. Compared to traditional techniques, chemical probes based on absorption or fluorescence changes are more feasible for detecting analyses owing to their many appealing advantages such as low detection limit, high selectivity, its real-time monitoring and its potential for vivo imaging of living cells.…”

Bottom-Up Hierarchical Self-Assembly of Chiral Porphyrins through Coordination and Hydrogen Bonds

“…To understand the role of metal ions and self-organization of porphyrins, enzymes and light-harvesting systems mimicking the natural pigments have been synthesized and studied, confirming the importance of the supramolecular structure on the light harvesting ability. [8][9][10][11][12] Self-assembled chiral systems based on synthetic porphyrins present a broad range of potential applications in areas such as photovoltaic cells, 13 sensors, 14 optoelectronics 15 and nanoelectronic devices 16 and also non-linear optical materials. 17 The number and position of the stereogenic centers in molecules united by covalent or non-covalent bonds directly affect the chiral transfer from the molecular level up to the supramolecular aggregates that they form in solution and consequently their optical activity can be modified.…”

Synthesis, characterization, aggregation-induced emission, solvatochromism and mechanochromism of fluorinated benzothiadiazole bonded to tetraphenylethenes

“…[3][4][5] Considering their potential use in optoelectronic devices such as organic light-emitting diodes (OLEDs), organic light-emitting eld-effect transistors (OLEFETs) and organic solid lasers, the molecules must exhibit high emission intensity in the solid state. However, conventional uorescent molecules exhibit relatively low uorescence in the solid state due to the strong aggregation caused quenching effect.…”