本研究合成含冠醚(monoaza-15-crown-5)以及二苯乙烯(stilbene)衍生物之螢光感測器(CN-Crown和H-Crown)，探討導入拉電子基團後對感測行為的影響，並比較兩者對金屬離子的選擇性和靈敏性。CN-Crown含有溴、氰基兩個拉電子基，H-Crown則只導入溴一個拉電子基。當加入不同金屬離子或改變金屬離子濃度時，螢光光譜會有明顯改變，並藉此探討其選擇性和靈敏性。由螢光光譜可觀察，只有導入強拉電子基的CN-Crown在不同極性溶劑中有定域化激發態(LE)-分子內電荷轉移態(ICT)的雙螢光現象，且隨著溶劑極性的增加，螢光光譜會有紅位移現象。CN-Crown對鋰離子有獨特的選擇性和高靈敏性(可偵測的最低濃度可以小於1 ppm)，而H-Crown則對鋰離子和鐵離子產生螢光萃熄。以鋰離子濃度滴定實驗可得到，相較於H-Crown (Ksv = 6.13×103 M-1)，CN-Crown (Ksv = 6.39×104 M-1)顯示出很高的靈敏性。電化學的探討則以循環伏安法(CV)求得HOMO與LUMO能階，發現導入強拉電子基的CN-Crown擁有較小的能隙。

To study the effect of electron-withdrawing group upon sensory characteristics of fluorescent chemosensors containing crown ether moiety (monoaza-15-crown-5), two stilbene derivatives CN-Crown and H-Crown were synthesized to compare their selectivity and sensitivity toward metal ions. CN-Crown contains two e-withdrawing groups (bromine and cyano) in stilbene unit, whereas H-Crown possesses bromine only. Fluorescence spectral variations in the presence of different metal ions or concentrations were used to elucidate the selectivity and sensitivity, respectively. CN-Crown displays dual fluorescence; where the short-wavelength emission (locally-excited state) mainly results from the stilbene group and the long-wavelength emission is attributed to the intramolecular charge transfer (ICT) process between electron-donor (amino) to electron-acceptor (stilbene unit). CN-Crown shows high selectivity toward Li+, while H-Crown is quenched not only by Li+ but also by Fe3+. The sensitivity of CN-Crown toward Li+ (Ksv = 6.39×104 M-1) is about one order higher than that of H-Crown (Ksv = 6.13×103 M-1). Clearly, e-withdrawing cyano group promotes ICT process in CN-Crown that results in its enhanced selectivity and sensitivity. In addition, incorporation of cyano group not only causes red-shift in fluorescence spectra but also leads to lower band gap in electrochemical property.

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