Key Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University , Hangzhou 310012, P. R. China.
J Org Chem. 2013 Nov 15;78(22):11318-25. doi: 10.1021/jo401808c. Epub 2013 Nov 7.
A series of donor-acceptor systems incorporating a carbazole moiety as the donating unit and pyridine moiety as the accepting unit have been designed and synthesized. The spectroscopic and electrochemical behaviors of the carbazole derivatives demonstrate that the carbazole unit interacts with the electron-accepting group through the π-conjugated spacer, thus leading to the intramolecular charge transfer (ICT). The pyridine-substituted carbazole derivatives show significant sensing and coordinating properties toward a wide range of metal cations. Compound S2 exhibits fluorescence enhancement upon association with transition metal cations, and compound V3 shows high selectivity for Cu(2+) among this series of materials. DFT calculations indicate the different association abilities of the dyes and the enhancement of ICT upon addition of the metal cations.
一系列供体-受体体系被设计和合成，其中包含咔唑部分作为供体单元和吡啶部分作为受体单元。咔唑衍生物的光谱和电化学行为表明，咔唑单元通过π共轭间隔基与电子受体相互作用，从而导致分子内电荷转移（ICT）。吡啶取代的咔唑衍生物对广泛的金属阳离子表现出显著的传感和配位性能。化合物 S2 与过渡金属阳离子结合后表现出荧光增强，而化合物 V3 在这一系列材料中对 Cu(2+)具有高选择性。DFT 计算表明，染料的不同结合能力以及加入金属阳离子后 ICT 的增强。
