Hydrophilic and photochromic switches based on the opening and closing of [1,3]oxazine rings

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Massimiliano TomasuloFrançisco M Raymo

Abstract

In search of strategies to operate photochromic compounds in aqueous environments, we synthesized two oxazines with a pendant oligo(ethylene glycol) chain each and a co-polymer with multiple oxazine and oligo(ethylene glycol) tails appended to a common macromolecular backbone. The hydrophilic character of the oligo(ethylene glycol) chains imposes solubility in water on two of the three systems. Their laser excitation in water opens the oxazine ring in less than 6 ns to generate zwitterionic isomers able to absorb in the visible region of the electromagnetic spectrum. The photogenerated species revert spontaneously back to the original forms with first-order kinetics. The transition from organic solvents to aqueous environments, however, causes a five-fold decrease in the quantum yield of the photoinduced ring-opening process and elongates the lifetime of the photogenerated isomer from the nanosecond to the microsecond domain. These hydrophilic and photochromic switches can be interconverted hundreds of times between their two states with no sign of degradation in water. As a result, our structural design for the realization of water-soluble photochromic compounds can lead to the development of viable strategies to modulate the ...Continue Reading

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Jun 25, 2009·Chemical Society Reviews·Ibrahim YildizFrançisco M Raymo

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Citations

Nov 10, 2012·The Journal of Physical Chemistry. a·Françisco M Raymo
Jun 28, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Yaroslav ProstotaJoão Seixas de Melo
Jun 23, 2012·Physical Chemistry Chemical Physics : PCCP·Erhan DenizFrançisco M Raymo
May 31, 2012·Chemistry : a European Journal·Janet CusidoFrançisco M Raymo
Jun 16, 2018·Chemical Communications : Chem Comm·Yang ZhangFrançisco M Raymo

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