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Photoswitchable basicity through the use of azoheteroarenes
| Title: | Photoswitchable basicity through the use of azoheteroarenes |
| Authors: | Fuchter, MJ |
| Item Type: | Dataset |
| Abstract: | Azoheteroarene photoswitches offer functional advantages over their more conventional azobenzene counterparts by virtue of their heteroaromatic ring(s). Here we report that azobis(2-imidazole) functions as a photoswitchable base due to the additional proton stabilisation that is possible in the protonated Z isomer, facilitated by the basic imidazole nitrogens. This thermodynamic difference in stability corresponds to a 1.3 unit difference in pKa values between the E and Z isomers. This pKa difference can be used to reversibly control solution pH. Azoheteroarene photoswitches offer functional advantages over their more conventional azobenzene counterparts by virtue of their heteroaromatic ring(s). Here we report that azobis(2-imidazole) functions as a photoswitchable base due to the additional proton stabilisation that is possible in the protonated Z isomer, facilitated by the basic imidazole nitrogens. This thermodynamic difference in stability corresponds to a 1.3 unit difference in pKa values between the E and Z isomers. This pKa difference can be used to reversibly control solution pH. |
| Issue Date: | 17-Dec-2015 |
| Citation: | 10.1039/C5CC10380K |
| URI: | http://hdl.handle.net/10044/1/44894 |
| DOI: | http://www.doi.dx.org/10.6084/m9.figshare.2975923 |
| Keywords: | Photoswitchable basicity azoheteroarenes |
| Appears in Collections: | Faculty of Natural Sciences - Research Data |
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