Luminescent Organogels Generated from Nucleosides Functionalized with Carbazole: Synthesis and Probing for F^–

Abstract

Novel luminescent organogelators based on nucleosides functionalized with carbazole (UC8, UC12 and UC16) were designed and synthesized. Their gelation ability was tested and it was found that both UC12 and UC16 could form stable organogels in toluene/petroleum ether. The UV/Vis absorption, fluorescence emission, and IR spectral changes during the gelation of UC12 proved that the self‐assembly was driven by hydrogen‐bonding. The morphology of the xerogel UC16 obtained from toluene/petroleum ether (v/v 1:1) displayed tough rod‐like microstructures, and 3D networks formed from numerous nanofibers were observed for the xerogel UC16 obtained from toluene/petroleum ether (v/v 2:1). It was interesting that the obtained organogels emitting blue light could be destroyed by the addition of F–, accompanied by a reduction of the emission intensity. Therefore, these organogels could be used as sensory materials to recognize F–.

Recently Developed Carbohydrate Based Gelators and Their Applications

“…Dephosphorylation of 92b generates compound 92a which was able to form a hydrogel at 0.8 wt % and Another example to show the use of nucleosides as functional organogels was researched by Jia et al This research showcased luminescent π-gelators. The gelators are soft materials with a wide variety of properties such as intense luminescence, charge carriers, and electronic conductivity [101]. The function of these gelators is commonly used in fluorescence imaging as well as chemo sensors.…”

“…A series of new π-gelators shown in Figure 53 below were synthesized by coupling alkyl carbazole with uridine [101]. These fluorescent nucleolipids could form organogels displaying different morphology in solvents such as toluene, and the driving forces for gelation included van der Waals force and hydrogen-bonding [101]. Another example to show the use of nucleosides as functional organogels was researched by Jia et al This research showcased luminescent π-gelators.…”

“…Nucleosides have been shown to exhibit good self-assembly directly correlated to hydrogen bonding. A series of new π-gelators shown in Figure 53 below were synthesized by coupling alkyl carbazole with uridine [ 101 ]. These fluorescent nucleolipids could form organogels displaying different morphology in solvents such as toluene, and the driving forces for gelation included van der Waals force and hydrogen-bonding [ 101 ].…”

Carbohydrate Derived Organogelators and the Corresponding Functional Gels Developed in Recent Time

“…Very recently, Jia et al have synthesized several nucleoside lipids based on uracil, attached at C-5 with N-alkylated (C8-, C12-, and C16-chains) carbazole, and studied the gelation of those [105]. Compounds having C12- and C16-alkyl chains formed stable organogels in toluene-petroleum ether.…”

Enantioselective Self-Assembled Nanofibrillar Network with Glutamide-Based Organogelator

“…In synthetic chemistry, chiral synthesis and chiral separation are still evolving as universal research tools, with supramolecular organogels attracting attention as media for chiral separation in recent years. Such gelation, unlike partially crosslinked polymer gelation, is characterized by the formation of a three-dimensional network through one-dimensional growth involving molecular aggregates of small chiral molecules, such as amino acids [ 2 , 3 , 4 , 5 ] and other chiral organic sources [ 6 , 7 , 8 , 9 ]. Therefore, such gels are very attractive in that they form highly ordered chiral orientations that are difficult to obtain using common polymer gels.…”