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Self-immolative colorimetric, fluorescent and chemiluminescent chemosensors

Chen Zhao
Chen Zhao
Department of Chemistry
University of Georgia
Chemistry Building, Room 400
Organic Seminar

Self-immolative chemistry has undergone rapid development in the past decades and led to molecular systems that possesses stimuli-responsive releasing properties. The unique self-immolative spacers serve as the fundamental component at these systems. They covalently link reagent-responsive group and a reporter moiety and can structurally “sacrifice” themselves in order to implement their designated function. The first self-immolative spacer was developed by the Katzenellenbogen group in 1981, which contained a 4-aminobenyl alcohol moiety that linked an enzyme substrate to a target reporter. Over more than 30 years, a variety of self-immolative spacers based on quionoe methide eliminations, azaquinone methide eliminations and cyclization reactions have been developed and shown promising applications in sensors, molecular amplifiers and stimuli-responsive materials. The design strategy of self-immolative chemosensors is modular which enables the self-immolative spacers to be applied to any sensor system. And self-immolative spacer could serve other functions in addition to just being a linker by providing incorporation between functional molecules and chemosensors. Continuing studies in this area will lead to the development in the design of functional molecular systems.

Reference:

  1. M. E. Roth, O. Green, S. Gnaim and D. Shabat, Chem. Rev.,2016, 116, 13091352.
  1. A. Alouane, R. Labrue`re, T. Le Saux, F. Schmidt and L. Jullien, Angew. Chem., Int. Ed., 2015, 54, 74927509.
  2. P. L. Carl, P. K. Chakravarty and J. A. Katzenellenbogen, J. Med. Chem., 1981, 24, 479480.
  1. S. Gnaim and D. Shabat, Acc. Chem. Res., 2014, 47, 29702984.

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