摘要
以o-dichlorophenyl為meso位置取代基之2,5-thienylene strapped [26]hexaphyrin (2) 的製備過程中分離出尚未發現的三環延伸紫質[18]thiaporphyrin[36]dithiaoctaphyrin[18]thiaporphyrin (3)。3是由2,5-thienylene所橋接的三環狀共軛系統所組成。2由X-ray單晶繞射結構鑑定出的鍵長和鍵角
，以及光譜資料皆符合文獻上以[18]thiaporphyrin和[26]hexaphyrin為框架之類似化合物的環電流造成的芳香性表現。3由X-ray單晶繞射所確認之固體結構為由扭曲的[36]dithiaoctaphyrin中心和兩個[18]thiaporphyrin朝向接近垂直包含中心主平面的側輪所組成。其扭角為170.3 o和171.3o，暗示可能為包含thiaporphyrins和dithiaoctaphyrin正交的π共軛系統。3在二氯甲烷呈現寬的吸收光譜符合[36]dithiaoctaphyrin的反芳香性特性。同時，在441 nm的吸收位置是由有芳香性的兩個[18]dithiaporphyrin所造成。pyrrole上質子在1H NMR光譜上的化學位移符合反芳香性的[36]dithiaoctaphyrin 和兩個芳香性的[18]thiaporphyrin pyrrole所造成的環電流效應之結果。

以UV–vis和螢光光譜儀偵測其對於不同金屬陽離子和陰離子的敏感性。分子感測器2,5-thienylene strapped [26]hexaphyrin (2 )對於Cu2+和Hg2+在MeOH /THF溶劑中表現高度的選擇性及靈敏度。其光譜顏色的改變主要在可見光區，用肉眼足以觀察。對於Cu2+和Hg2+在MeOH/THF溶劑中的偵測極限分別為1.978µM和1.283µM，對於F-在dichloromethane中偵測極限為1.052µM。化學感測器2對Cu2+和Hg2+的1:1錯合物和F-的1:2錯合物表現出吸收回饋。
分子感測器[18]thiaporphyrin[36]dithiaoctaphyrin[18]thiaporphyrin (3)在MeOH/THF溶劑中可偵測Cu2+、Hg2+和Pd2+。3對於Cu2+、Hg2+和Pd2+在MeOH/THF溶劑中的偵測極限分別為0.3 µM、1.55 µM 和 0.7 µM (3α/slope)。分子感測器3於Cu2+、Hg2+和Pd2+的分別有1:2、1:3和1:4的鍵結當量。

The introducing of the o-dichlorophenyl group as the meso substituent for the preparation of 2,5-thienylene strapped [26]hexaphyrin (2) isolated an unprecedented tricyclic expanded porphyrin, [18]thiaporphyrin[36]dithiaoctaphyrin[18]thiaporphyrin (3). 3 comprises of three conjugation ring systems fused through the 2,5-thienylene bridging moiety. The bond distances and bond angles from the X-ray single-crystal structural determination as well as other spectroscopic data of 2 are in line with its literature reported congeners, which show the contribution of aromaticity from ring currents of both [18]thiaporphyrin and [26]hexaphyrin frameworks. The solid-state structure of 3 revealed by X-ray single crystal diffractometer confirms a distorted [36]dithiaoctaphyrin central core with two [18]thiaporphyrin sidewheels oriented near perpendicular to the mean plane of the central core with torsion angles of 170.3 and 171.3o, likely implying orthogonal π-conjugation systems among thiaporphyrins and dithiaoctaphyrin. The broad absorption spectrum of 3 in CH2Cl2 is consistent with the presence of an anti-aromatic [36]dithiaoctaphyrin core. Meanwhile, a distinctive absorption band at 441 nm suggests that the absorption spectrum is dominated by the aromaticity of two [18]dithiaporphyrin units. The chemical shifts of 1H NMR spectrum of 3 are in agreement with the effects of paratropic ring current exerted on protons at the pyrrolic protons of the anti-aromatic [36]dithiaoctaphyrin and under the influences of the diatropic ring current to protons on pyrrolic protons of two aromatic [18]thiaporphyrin sidewheels.
The sensing of (2) behavior toward various metal ions and anions was investigated by UV–vis and fluorescence spectroscopic techniques. The molecular sensor 2,5-thienylene strapped [26]hexaphyrin (2 ) exhibited a highly selective and sensitive colorimetric response to Cu2+ and Hg2+ in MeOH /THF. The spectral changes obtained are large enough in the visible region of the spectrum and thus enable naked-eye detection. The detection limit of Cu2+ and Hg2+ for this chemo-sensor in MeOH/THF solution was 1.978 and 1.283 µM respectively and 1.052 µM for F- in dichloromethane. Chemosensor 2,5-thienylene strapped [26]hexaphyrin (2 ) shows with absorption responses both Cu2+ and Hg2+ a 1:1 complexes and a 1:2 complex with F- ion.
The molecular sensor [18]thiaporphyrin[36]dithiaoctaphyrin[18]thiaporphyrin (3) detected Pd2+ in MeOH/THF in addition to Cu2+and Hg2+. The detection limit of Cu2+, Hg2+, and Pd2+ for 3 in MeOH/THF solution was 0.3 µM, 1.55 µM, and 0.7 µM, respectively based on 3α/slope. Molecular sensor 3 shows with absorption responses 1:2, 1:3, and 1:4 binding stoichiometry with Cu2+, Hg2+, and Pd2+, respectively.

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