New fluorescent bis‐β‐cyclodextrin‐indolizine sensor. Synthesis and sensing ability

Abstract

The synthesis of 1,3‐[bis‐N‐6A‐deoxy‐β‐cyclodextrin‐6A‐yl‐aminocabonyl]‐7‐pyridin‐4‐yl indolizine is reported. The reaction proceeds by an amidation between 6‐amino‐β‐cyclodextrin and 1,3‐[bis‐(‐4‐nitrophenoxycarbonyl)‐7‐[pyridine‐4‐yl)] and yields the first sensor having in its structure the fluorescent indolizine and two β‐cyclodextrin fragments. The sensing ability towards phenol, p‐cresol and adamantan‐1‐ol has been evaluated by fluorescence spectroscopy. The molecular modelling study realised by MM3 and AM1 methods shows that non cooperative conformations are favoured, thus explaining that inclusion ability is not increased by such dimer, and that sensitivity is not enhanced as compared to corresponding monomeric sensors.

Fluorescent Indolizine-b-Cyclodextrin Derivatives for the Detection of Volatile Organic Compounds

“…Thus, we have synthetised the 1,3-[bis-N-6A-deoxy-β-cyclodextrin-6A-yl-aminocarbonyl]-7-pyridin-4-yl indolizine (Scheme 2) as a part of our outgoing research program to develop a new range of fluorescent β-CD sensors [29]. …”

Iodine-Promoted Synthesis of 3-Arylindolizine-1-Carboxylates from 2-(2-Nitro-1-Arylethyl)Malonates and Pyridine

“…IR spectra were recorded in a Nicolet FT-IR 5DX spectrometer. The 1 H NMR (600 MHz) and 13 C NMR (150 MHz) spectra were recorded in a Bruker AV-600 spectrometer with TMS as internal reference in CDCl 3 solutions. J values are given in Hz.…”

“…Although, there are several methods for the preparation of the polysubstituted indolizine derivatives, most current procedures involve multistep. [8][9][10][11][12][13][14] The development of efficient methods for the synthesis of polysubstituted indolizine derivatives requires attention.…”

A competitive sensing system based on cyclobis(paraquat-p-phenylene) and a new β-cyclodextrin-tetrathiafulvalene derivative

“…Thus, such derivatives might lead to molecule-sensing systems [8][9][10][11][12][13]. Especially, we have developed a new class of fluorescent sensors towards volatile organic compounds (VOC), by coupling a βcyclodextrin fragment (β-CD) with indolizine units [14][15][16][17][18][19]. On the other hand, the sensing of anions or metallic cations may be realised by means of electrochemical sensors based on tetrathiafulvalene (TTF) and various receptors such as crown ethers, calixarenes or calyxpyrroles [20][21][22][23][24][25].…”