在本論文中，我們致力於開發有效的多環稠合共平面之-二酮的合成方法，並作為合成含吡嗪共軛結構的關鍵單元。至目前為止，我們已成功合成出兩種多環稠合共平面之-二酮的異構物(化合物9與化合物33)， 並利用這類已開發成功的-二酮作為前驅物合成了數個小型模型染料分子。 我們對這些新開發的染料分子進行線性和非線性光學測量，並發現了以下特點： [1] 當在模型分子中引入雜環單元(如:吡啶、塞酚)會使得分子之吸收峰與螢光放射峰產生紅移,但量子產率也會隨之降低。 [2] 增加推電子基的數量對於吸收與螢光的強度及雙光子吸收截面皆有正面幫助,但對於吸收峰與螢光放射峰的位置並沒有正相關。 [3] 提升分子共平面性有助於增加分子之吸收峰與螢光放射峰紅移程度。 [4] 在兩種-二酮的異構物當中,使用彎曲型的-二酮(化合物33)所構成的染料結構有更紅移的吸收峰與螢光放射峰 ;In this thesis, we attempted to develop efficient synthetic procedure toward polycyclic and coplanar -diketones as the key synthons for various pyrazine-containing conjugation structures. So far, we have successfully constructed the desired -diketones and have synthesized several small model compounds based on these developed -diketone isomers. We have performed linear and non-linear optical property measurements on these newly synthesized chromophors and have found out the following features: [1] When a heterocyclic unit( i.e. pyridine and thiophene) is introduced into this model system, the absorption peak of the molecule and the fluorescence emission peak are red-shifted, but the quantum yields are decreased. [2] Increasing the number of electron-donating groups can enhance the intensity of absorption and fluorescence as well as two-photon absorptivities. [3] Increasing the coplanarity of the molecule helps to increase the extent of red-shift about absorption peak and fluorescence emission peak. [4] For the isomeric structures, the one constructed by using bent-shaped -diketone as the precursor manifests relatively red-shiftted absorption and emission bands.
