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Synthesis and exploring the excited-state PES of photochromic hydrogen bond-assembled [2]rotaxane based on 1,3-Diazabicyclo-[3.1.0]hex-3-enes

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Abstract

Here, the synthesis of photochromic hydrogen bond-assembled [2]rotaxanes using bis-fumarate as a thread for the first time is reported. In fact, photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene moieties were used as stoppers and two-atom spacers managed good binding sites for the tetralactam macrocycles in clipping reactions. Moreover, the yields of photochromic [2]rotaxanes highly depended on the NO2 substituent stoppers. While the thread with a para –NO2 substituent as stopper units was shown to be an excellent template for the synthesis of photochromic [2]rotaxanes. The structures of the [2]rotaxanes are established clearly in solution by chemical shifts of the 1H 13C NMR signals and UV–Vis spectra. A pronounced bathochromic shift was occurred in the excitation wavelength of photochoromic [2]rotaxanes compared with the absorption band of photochromic threads. Therefore, these organizations can be applied in light-driven molecular switches and motors. The reversible transformation of trans and cis geometric photoisomers under UV radiation was identified. In other efforts, the possibility of the process of trans to cis interconversion of the fumarate linker under UV irradiation has been examined computationally and it has appeared that it may cause the transverse of the bis-fumarate linker inside the tetralactam macrocycle to some extent.

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Acknowledgements

The authors express appreciation to University of Guilan, Faculty Research Committee for support of this investigation.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Guilan, P.O. Box 41335-1914, Rasht, Iran

    Nosrat O. Mahmoodi & Farhad Shirini

  2. Department of Chemistry, University of Guilan, University Campus 2, P.O. Box 41335-1914, Rasht, Iran

    Mostafa Fasihi-Ramandi

  3. Department of Chemistry, Razi University, P.O. Box 6714967346, Kermanshah, Iran

    Atefeh Ghavidast

  4. Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran

    Hossein Taherpour Nahzomi

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  1. Mostafa Fasihi-Ramandi
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Correspondence to Nosrat O. Mahmoodi or Atefeh Ghavidast.

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Fasihi-Ramandi, M., Mahmoodi, N.O., Ghavidast, A. et al. Synthesis and exploring the excited-state PES of photochromic hydrogen bond-assembled [2]rotaxane based on 1,3-Diazabicyclo-[3.1.0]hex-3-enes. Res Chem Intermed 47, 2557–2572 (2021). https://doi.org/10.1007/s11164-021-04425-7

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