Coordination Driven Capture of Nicotine Inside a Mesoporous MOF.

Davide Balestri,Nicola Demitri,Paolo Pelagatti,Davide Capucci,Alessia Bacchi

doi:10.3390/ma10070727

Davide Balestri, Nicola Demitri + Show 3 more

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https://doi.org/10.3390/ma10070727

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Abstract

Metal organic frameworks (MOFs) are a wide class of crystalline porous polymers studied in many fields, ranging from catalysis to gas storage. In the past few years, MOFs have been studied for the encapsulation of organic or organometallic molecules and for the development of potential drug carriers. Here, we report on the study of two structurally-related mesoporous Cu-MOFs, namely PCN-6 and PCN-6′ (PCN stands for Porous Coordination Network), for nicotine trapping. Nicotine is a well-known alkaloid liquid molecule at room temperature, whose crystalline structure is still unknown. In this work, the loading process was monitored by electron ionization mass spectrometry by using a direct insertion probe (DIP-EI/MS), infrared (IR), and ultraviolet/visible (UV/VIS) analysis. Both nuclear magnetic resonance (NMR) spectroscopy and thermogravimetric (TGA) analysis showed evidence that nicotine trapping reaches remarkable uptakes up to 40 wt %. In the case of PCN-6@nicotine, X-ray structural resolution revealed that the guest uptake is triggered by coordination of the pyridine ring of nicotine to the copper nuclei of the paddle-wheel units composing the framework of PCN-6.

Highlights

Nicotine is a natural chiral alkaloid which is contained in tobacco leaves, approximately0.6–3.0% of the dry plant weight
Since nicotine can be considered as a liquid active pharmaceutical ingredient (API), it is highly desirable to find some method to stabilize it in crystalline form
Discussion network2.and the and characterization of the derived material based on nuclear magnetic resonance (NMR), thermogravimetric (TGA), 2.1

Summary

Introduction

It functions as a natural anti-herbivore agents in some Solanaceae, such as aubergine and tomato [1]. For this reason, until the middle of 20th century, nicotine found a broad use as an insecticide in different formulations [2,3]. Since nicotine can be considered as a liquid active pharmaceutical ingredient (API), it is highly desirable to find some method to stabilize it in crystalline form. Metal organic frameworks (MOFs) are a relatively new class of porous crystalline materials, deriving from the self-assembly of metal ions or metal aggregates (SBU = secondary building units) with organic linkers [8].

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