The para-sulfonamide analogue (p-TsABDI) of green fluorescent protein (GFP) chromophore was prepared by treating the para-amino analogue (p-ABDI) of GFP chromophore with 1.2 equivalents of tosyl chloride in the presence of NEt3. In the solvents of DMSO and acetonitrile, p-TsABDI partially protonates the dipolar aprotic solvents and causes excited-state proton transfer (ESPT). Its ground-state pKa value in DMSO was calculated to be 6.7, and its S1 excited-state pKa* value in DMSO was calculated to be -1.5. In comparison with 8-hydroxypyrene-1,3,6-trisulfonate (HPTS) (pKa = 7.4, pKa* = 1.3 in water), p-TsABDI would be a good photoacid for pH-jump studies. We will show the details in the symposium.

Para-sulfonamide analogue of green fluorescent protein chromophore: Excited-state proton transfer

2019 Spring National Meeting

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