A novel pillar[5]arene-based supramolecular organic framework gel to achieve an ultrasensitive response by introducing the competition of cation⋯π and π⋯π interactions

Abstract

Ultrasensitive response properties are an intriguing concern for stimuli-responsive materials. Herein, we report a novel method to achieve an ultrasensitive response by introducing the competition of cationπ and ππ interactions into a pillar[5]arene-based supramolecular organic framework (SOF-AMP). SOF-AMP was constructed with a novel bis-naphthalimide functionalized pillar[5]arene, which was able to form a stable supramolecular gel (SOF-AMP-G) in cyclohexanol. Interestingly, SOF-AMP-G shows an ultrasensitive response to Fe3+ through the competition of cationπ and ππ interactions. Meanwhile, the Fe3+ coordinated SOF (MSOF-Fe) shows an ultrasensitive response to H2PO4-. SOF-AMP-G displayed yellow fluorescence whereas, after the addition of 0.5 equiv. of Fe3+ to SOF-AMP-G, the yellow fluorescence was quenched. The detection limit of SOF-AMP-G for Fe3+ is 7.54 × 10-9 M. More interestingly, the Fe3+ coordinated SOF gel (MSOF-Fe-G) could sense H2PO4- with a fluorescence "turn-on". The detection limit of MSOF-Fe-G for H2PO4- is 4.21 × 10-9 M. Simultaneously, the Fe3+ and H2PO4- responsive thin films based on these SOF gels were prepared. Moreover, these SOF gels could be used as ultrasensitive ion sensors, fluorescent display materials and sensitive logic gates.

Supramolecular Aggregation-Induced Emission Gels Based on Pillar[5]arene for Ultrasensitive Detection and Separation of Multianalytes

“…In our previous works, we have synthesized compound H, P, D, and DP. 49,50 These synthesis procedures are depicted in Schemes 1 and S1. A mixture of bromofunctionalized pillar [5]arene (PM) (0.95 g, 1.0 mmol) and phthalimide potassium (0.37 g, 2.0 mmol) in DMF solution (30 mL) was stirred at 90 °C for 24 h under nitrogen atmosphere.…”

A pH-Responsive Supramolecular Drug Delivery System Constructed by Cationic Pillar[5]arene for Enhancing Antitumor Activity

“…pillar [n]arenes, as a new class of macrocycle first synthesized by Ogoshi et al (2008), have recently been widely used in many fields including molecular recognition (Yakimova et al, 2016;Yuan et al, 2017), mechanical interlocking molecules (Chen et al, 2013a;Zhang et al, 2019c), artificial transmembrane channels (Chen et al, 2013b;Xin et al, 2017), metal ion separation (Xia et al, 2017), chemical sensors (Wu et al, 2014;Stepanova et al, 2017;Wei et al, 2017;Hua et al, 2018;Sun et al, 2018), and supramolecular polymers (Strutt et al, 2012;Zhou et al, 2014a;Nierengarten et al, 2016;Zhang et al, 2018). At present, researchers are more focusing on the study of watersoluble pillar [n]arenes (Hu et al, 2016;Yang et al, 2016;Yu et al, 2016;Zhou et al, 2017b;Li et al, 2019;Zhong et al, 2019) because they can effectively bind different types of molecules into their cavities to construct a series of stimulus-responsive supramolecular amphiphiles for the application in DDSs.…”

Understanding of supramolecular solution polymerization and interfacial polymerization via forming multiple hydrogen bonds: a computer simulation study

“…Supramolecular polymers refer to chain-like aggregates of monomers linked by non-covalent bonds, which are held together by highly directional secondary and reversible interactions and possess polymeric properties in solution and in bulk. 1,2 The non-covalent bonds can be multiple hydrogen bonds, [3][4][5][6][7][8] p-p interactions, [9][10][11][12][13][14] host-guest interactions [15][16][17][18][19][20] and metal coordination interactions. [21][22][23][24][25] Supramolecular polymers have self-healing, degradable, and regenerative properties, which are often used to design responsive, self-healing, and environmentally friendly materials.…”