Acid/Base and H2PO4鈥?Controllable High-Contrast Optical Molecular Switches with a Novel BODIPY Functionalized [2]Rotaxane

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• 作者：Reguram Arumugaperumal ; Venkatesan Srinivasadesikan ; Mandapati V. Ramakrishnam Raju ; Ming-Chang Lin ; Tarun Shukla ; Ravinder Singh ; Hong-Cheu Lin
• 刊名：ACS Applied Materials & Interfaces
• 出版年：2015
• 出版时间：December 9, 2015
• 年：2015
• 卷：7
• 期：48
• 页码：26491-26503
• 全文大小：805K
• ISSN：1944-8252

文摘

A novel multifunctional mechanically interlocked switchable [2]rotaxane R4 containing two molecular stations and rotaxane arms terminated with boron-dipyrromethene (BODIPY) fluorophores and its derivatives were synthesized for the first time by CuAAC click reaction. The shuttling motion of macrocycle between the dibenzylammonium and triazolium recognition sites and the distance dependent photoinduced electron transfer process of R4 is demonstrated by utilizing external chemical stimuli (acid/base). Interestingly, the reversible self-assembly process of R4 was recognized by the acid鈥揵ase molecular switch strategy. Notably, two symmetrical triazolium groups acted as molecular stations, H₂PO₄^{鈥?/sup> receptors, and H-bonded donors. Both [2]rotaxane R4 and thread R2 demonstrated excellent optical responses and high selectivity toward H₂PO₄鈥?/sup> ion. The specific motion and guest鈥揾ost interactions of mechanically interlocked machines (MIMs) were also further explored by quantum mechanical calculations. The thread R2 also demonstrated to enable the detection of H₂PO₄鈥?/sup> in RAW 264.7 cells successfully.}