本研究主要藉由程序控溫反應/脫附(temperature-programmed reaction/desorption, TPR/D)、反射式吸收紅外光譜 (reflection-absorption infrared spectroscopy, RAIRS)、X-光光電子光譜 (x-ray photoelectron spectroscopy, XPS) 探討在超高真空系統中，雙官能基分子，HOCH2CH2NH2、ICH2COOH與ICH2CN，在Cu(100)表面上的吸附以及熱反應，再藉由密度泛函理論 (density functional theory, DFT) 預測反應中間物之結構以及可能的反應路徑和能量。
Cu(100)表面上，單層與多層的HOCH2CH2NH2分子脫附峰溫度分別為255與203 K。由RAIRS結果推測多層與單層分子可能以不同的HOCH2CH2NH2 旋轉異構物形式吸附於Cu(100)表面。於 ~240 K時，脫附與分解會同時發生。HOCH2CH2NH2在Cu(100)表面上的分解路徑，可能是先失去一個氫原子而形成-OCH2CH2NH2，接著再轉變成HOCH2CH2N=。這個HOCH2CH2N=中間物約在400 K分解生成H2與H2O。
ICH2COOH在230 K的Cu(100)表面上會分解產生CH2COO與CH3COO，增溫至300 K時，所有的CH2COO會轉變成CH3COO，這是CH2COO與羧酸斷O-H鍵所生之表面H結合的產物。CH3COO於550 K以上會分解成-C≡COH表面中間物以及脫附H2、CH4、H2O、CO、 CO2、CH2CO、與 CH3COOH等氣相產物，密度泛函理論計算預測 CH2COO 吸附結構之 CCOO 平面幾乎與表面平行並且CCOO骨架上有delocalized π電子。-C≡COH吸附於bridge與hollow site的穩定性相似並且CCO分子軸基本上垂直於表面。-C≡COH於600-700 K之間會再分解產生H2與CO。
ICH2CN在Cu(100)表面上的分解可得CH2CN、CHCN、CCN和CN的表面中間物。這些表面物種的存在和反應導致下列分子的脫附：H2、HCN、CH3CN與C2N2。CH3CN呈現複雜脫附形態，是來自CH2CN的不勻稱 (disproportiontion) 與氫化反應。HCN的形成是多個基本反應步驟的產物 (CHCN → CCN + H → CCHN → C + HCN)。C2N2形成機制則是CCN斷C-C鍵而產生C與CN，然後CN(a)再偶合。理論計算預測低覆蓋率的CH2CN與CHCN之吸附結構皆以CCN骨架幾乎與表面平行。

The adsorption and thermal chemistry of the bifunctional molecules, HOCH2CH2NH2, ICH2COOH and ICH2CN, on Cu(100) have been studied in ultra-high vacuum system by a combination of temperature-programmed reaction/desorption (TPR/D), reflection-absorption infrared spectroscopy (RAIRS), and X-ray photoelectron spectroscopy (XPS), with the aid of theoretical calculations based on density functional theory for prediction of reaction intermediate structures, reaction paths and eneretics.
In the case of HOCH2CH2NH2 on Cu(100), the molecular desorption from the multilayer and monolayer occurs at 203 and 255 K, respectively. The HOCH2CH2NH2 molecules present in the multilayer and monolayer are adsorbed with different conformations. Desorption and decomposition of HOCH2CH2NH2 molecules on Cu(100) can occur at ~ 240 K simultaneously. In the decomposition process of HOCH2CH2NH2 on Cu(100), it may first lose a hydrogen atom to form -OCH2CH2NH2, which then transforms into HOCH2CH2N=. Further decomposition of HOCH2CH2N= at ~400 K results in the desorption of H2 and N2.
ICH2COOH decomposes on Cu(100) at 230 K into the surface intermediates of CH2COO and CH3COO. As the surface is heated to 300 K, all the residual CH2COO molecules change to CH3COO, which is the result due to recombination of CH2COO with the H atoms from deprotonation of the -COOH group. CH3COO decomposes at ~550 K to produce CCOH surface intermediate and the gaseous products of H2, CH4, H2O, CO, CO2, CH2CO and CH3COOH. CCOH decomposes to generate H2 and CO2 at 600-700 K. CH2COO, with a delocalized π-system, is predictes to be adsorbed with the skeletal CCOO plane approximately parallel to the surface. -C≡COH adsorbed on the bridge site and hollow site has a similar stability, with molecular CCO axis is basically perpendicular to the surface.
On Cu(100), ICH2CN decomposes to generate the surface intermediates: CH2CN, CHCN, CCN and CN. The further reactions of these surface species lead to the desorption of CH3CN, H2, HCN and C2N2. CH3CN show a complex desorption behavior form CH2CN disproportionation and hydrogenation. HCN is a resultant product of multiple elemental steps: CHCN → CCN + H → CCHN → C + HCN. C2N2 result from recombination of CN groups which is the reaction product of CCN by C-C bond scission. Both the CH2CN and CHCN are predicted to be adsorbed with the CCN backbones approximately parallel to the surface at a low conerage.

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