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Supramolecular photochemistry of encapsulated caged ortho-nitrobenzyl triggers†

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Abstract

ortho-Nitrobenzyl (oNB) triggers have been extensively used to release various molecules of interest. However, the toxicity and reactivity of the spent chromophore, o-nitrosobenzaldehyde, remains an un-addressed difficulty. In this study we have applied the well-established supramolecular photochemical concepts to retain the spent trigger o-nitrosobenzaldehyde within the organic capsule after release of water-soluble acids and alcohols. The sequestering power of organic capsules for spent chromophores during photorelease from ortho-nitrobenzyl esters, ethers and alcohols is demonstrated with several examples.

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Authors and Affiliations

  1. Department of Chemistry, University of Miami, 33146, Coral Gables, FL, USA

    Nareshbabu Kamatham, A. Mohan Raj & V. Ramamurthy

  2. Department of Chemistry, University of Kansas, 66045, Lawrence, KS, USA

    Richard S. Givens

  3. CCMAR – Centre of Marine Sciences, University of Algarve, 8005-139, Campus de Gambelas, Faro, Portugal

    José P. Da Silva

Authors
  1. Nareshbabu Kamatham
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  2. A. Mohan Raj
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  3. Richard S. Givens
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  4. José P. Da Silva
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  5. V. Ramamurthy
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Corresponding author

Correspondence to Nareshbabu Kamatham.

Additional information

Electronic supplementary information (ESI) available: Experimental procedures, 1H NMR, UV and ESI-MS spectra for all new compounds. Irradiation procedures, 1H NMR titration spectra of host–guest complexes, progress of photoreactions as monitored by 1H NMR, LC-DAD-MS. See DOI: 10.1039/ c9pp00260j

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Kamatham, N., Raj, A.M., Givens, R.S. et al. Supramolecular photochemistry of encapsulated caged ortho-nitrobenzyl triggers†. Photochem Photobiol Sci 18, 2411–2420 (2019). https://doi.org/10.1039/c9pp00260j

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  • DOI: https://doi.org/10.1039/c9pp00260j

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