2018
DOI: 10.1021/acs.joc.7b02604
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Abstract: The electronic and steric effects of aryl substituents and the influence of hydrogen bonding in Z-isomer stability of phenylazopyrazole derivatives have been investigated. In this regard, 38 substituted phenylazopyrazole derivatives and 6 N-methyl phenylazopyrazoles (with meta substitutions) have been synthesized. Their photoswitching behavior, photostationary states (PSS), and kinetics of thermal reverse isomerization were evaluated experimentally using UV-vis and NMR spectroscopic techniques. Furthermore, de… Show more

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Cited by 58 publications
(82 citation statements)
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“…Even at a very high concentration (1.6 m m ), the E – Z isomerization was found to show 40 % isomerization (Supporting Information, Figure S1). This clearly supported our understanding, based on the earlier studies on azopyrazoles, that the photoisomerization step can be limited by hydrogen bonding . Surprisingly, the 2‐hydroxy‐ and 2‐amino‐substituted derivatives ( 12 d and 32 d , respectively) were also found to undergo photoswitching.…”
Section: Resultssupporting
confidence: 88%
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“…Even at a very high concentration (1.6 m m ), the E – Z isomerization was found to show 40 % isomerization (Supporting Information, Figure S1). This clearly supported our understanding, based on the earlier studies on azopyrazoles, that the photoisomerization step can be limited by hydrogen bonding . Surprisingly, the 2‐hydroxy‐ and 2‐amino‐substituted derivatives ( 12 d and 32 d , respectively) were also found to undergo photoswitching.…”
Section: Resultssupporting
confidence: 88%
“…In spite of significant changes in those parameters, the computed structural data did not show any trend that can account for the electronic effects of the substituents. In fact, this observation was also made in the case of arylazopyrazoles with meta substituents . Likewise, in our earlier studies on arylazopyrazoles, the inspection of molecular orbitals corresponding to HOMO−1, HOMO, and LUMO of the E‐ isomers of phenylazoisoxazole revealed n, π, and π* orbitals, respectively.…”
Section: Resultssupporting
confidence: 74%
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