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<p>In this work, the excited state intramolecular proton transfer (ESIPT) behavior of (<i>E</i>)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DH) and 2-(5-(4-(dimethylamino)phenyl)-4,5-dihydro-1<i>H</i>-pyrazol-3-yl)phenol (DDP) was systematically investigated using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. The analysis of bond critical point parameters and potential energy curves confirmed the occurrence of ESIPT in the excited states of both DH and DDP. This finding is consistent with the dual fluorescence emission observed experimentally for DH and DDP. Through this comprehensive investigation, we elucidated the fluorescence mechanism of DH for detecting N<sub>2</sub>H<sub>4</sub>. Furthermore, the ESIPT behavior of two additional compounds, (<i>E</i>)-3-(4-(di-<i>p</i>-tolylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (TAPHP), and 2-(5-(4-(di-<i>p</i>-tolylamino)phenyl)-4,5-dihydro-1<i>H</i>-pyrazol-3-yl)phenol (TAPDP), was also examined. This was motivated by the structural similarity between TAPHP and DH, as well as their shared detection mechanism for N<sub>2</sub>H<sub>4</sub>. The results revealed that only TAPDP exhibits ESIPT behavior in its excited state. Additionally, it was determined that the electron-donating effect and the extent of the conjugated system, influenced by different substituents, play a crucial role in modulating the ESIPT behavior of (<i>E</i>)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one.</p>

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Insights into the fluorescence mechanism of a dual-signal probe based on α, β-unsaturated carbonyl group for detecting hydrazine

  • 期刊论文

  • 发表日期：

    2025年4月21日

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  • Lei Wang,
  • Lulu Dong,
  • Jiajia Wu,
  • Tiancheng Xiang,
  • Wenjing Zhang,
  • Ruihong Duan

摘要

In this work, the excited state intramolecular proton transfer (ESIPT) behavior of (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DH) and 2-(5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (DDP) was systematically investigated using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. The analysis of bond critical point parameters and potential energy curves confirmed the occurrence of ESIPT in the excited states of both DH and DDP. This finding is consistent with the dual fluorescence emission observed experimentally for DH and DDP. Through this comprehensive investigation, we elucidated the fluorescence mechanism of DH for detecting N2H4. Furthermore, the ESIPT behavior of two additional compounds, (E)-3-(4-(di-p-tolylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (TAPHP), and 2-(5-(4-(di-p-tolylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (TAPDP), was also examined. This was motivated by the structural similarity between TAPHP and DH, as well as their shared detection mechanism for N2H4. The results revealed that only TAPDP exhibits ESIPT behavior in its excited state. Additionally, it was determined that the electron-donating effect and the extent of the conjugated system, influenced by different substituents, play a crucial role in modulating the ESIPT behavior of (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one.