臺灣博碩士論文加值系統

含溴基之柳醛化合物與炔類經由Sonogashira耦合反應可得到新穎含炔基柳醛化合物201-203。將柳醛化合物與醋酸鋅作用，再加入相對應的雙胺化合物可以合成一系列的鋅金屬席夫鹼錯合物204-214和217-230。三核錯合物215是利用錯合物208與trans-Pd(PnBu3)2Cl2反應所得到，而將215與氰化銀作用則可得到含氰基的三核錯合物216。我們也研究了上述所提到之此類新化合物的光物理性質。導入一個pyridine基作為架橋單元可大幅提昇其螢光強度及量子產率。另外，在柳醛基上加入炔基與推電子基亦可提昇其螢光強度及量子產率。電子豐盈的金屬基團鈀基團的確會增加其放光之物理特性，推測可能是經由三鍵的作用。單核二價鎳席夫鹼錯合物232與其多核錯合物233和234也是利用類似合成鋅金屬系統的方法所製備。
Pyridine雙亞銨化合物301是利用縮合反應製備。將化合物301乙炔化之後可得到含雙炔之配位基302。以CuCl為催化劑，將302與trans-Pd(PR3)2Cl2反應可得到雙鈀金屬錯合物303a和303b。多核錯合物304a和304b則是利用CuI催化所得到。錯合物305—307是由303製備而來，而且具有四個鈀金屬尾端的八面體物種306以及307可能作為互鎖超分子上的一個構築區塊。在乙醇與二氯甲烷的混和物中，304a與鋅金屬鹽類作用後可得到異金屬聚合物308。具有較大立體阻礙雙炔化合物310是經由一連串類似合成302的步驟所得到。將兩個尾端pyridine加入310的骨架中可形成第一個具有雙pyridine取代基的pyridine雙亞銨311。將311與Re(CO)5Br更進一步反應則可得到中性的Re(I)聚合物312，而未得到自組裝產物，此結果是由不適當的鍵結形狀所造成的。

Novel alkyne-substituted salicylaldehydes 201-203 are prepared via Sonogashira coupling reaction. A series of Zn Schiff base complexes 204-214 and 217-230 are obtained by a new method that the salicylaldehydes are first treated with zinc acetate followed by addition of the corresponding amines. Trinuclear complex 215 is obtained by reaction of 208 with trans-Pd(PnBu3)2Cl2, and the reaction of 215 with AgCN gives a cyano-substituted trinuclear complex 216. Photophysical properties of these new compounds mentioned above are investigated. Introduction of a pyridyl group as a bridging unit enhances the fluorescence intensity and quantum yield significantly. Additionally, incorporation of ethynyl and electron-donating groups into salicylidene moiety also enhances the fluorescence intensity and quantum yield. Electron-rich palladium groups indeed enhance the luminescence in photophysical character possibly through the C≡C bond. The mononuclear Ni(II) Schiff base complex 232 and its multinuclear complexes 233 and 234 are prepared using the similare method for the Zn system.
2,6-Diacetylpyridinebis(4-iodoanil) (301) is prepared via condensation. The ethynylation of 301 is achieved leading to the formation of diyne ligand 302. Treatment of 302 with trans-Pd(PR3)2Cl2 using CuCl as catalyst gave dipalladium complexes 303a and 303b. Polynuclear complexes 304a and 304b are also obtained in the presence of catalytic amount of CuI. Complexes 305—307 are prepared from 303, and the octahedral species 306 and 307 containing tetra Pd terminus could be used as a building block in the interlocked supramolecules. Reaction of 304a with zinc salt in a mixture of ethanol/CH2Cl2 affords polymeric heterometallic 308. The more hindered 2,6-bis(imino)pyridyl diyne ligand 310 is obtained by a series of synthetic procedures similar to those of 302. Incorporation of two terminal pyridyl groups into the backbone of 310 is achieved leading to the formation of the first dipyridyl-substituted pyridine dimine 311. Further reaction of 311 with Re(CO)5Br produces the neutral Re(I) polymer 312 instead of a self-assembly product due to inappropriate bonding geometry.

Chapter 1 Introduction 1
Organometallic Polymers with Transition Metals in the Main Chain 1
Transition Metal—Acetylide Complexes 3
I. Synthesis of Polymers 3
II. Bonding Property of Polymers 8
III. General Properties of Polymers 9
a. Stability 9
b. Solution Properties 10
c. Liquid Crystalline Properties 10
d. Optical Spectroscopy 11
e. Nonlinear Optical Properties 13
f. Electrochemical and Electrical Properties 14
Distinctive Alkynylated Schiff Bases 15
Scopes for Research 17
References 18
Chapter 2 Novel Zn(II) and Ni(II) Schiff Base Complexes
and Their Photophysical Properties 24
Background 24
I. Electroluminescent (EL) materials 24
II. Applications of Bis(salicylidene)diamine Complexes
in Catalysis 31
III. Optoelectronic Properties of Metal Schiff Base
Complexes and Their Applications 35
Result and Discussion 40
I. Synthesis of 5-Substituted Salicylaldehyde 40
II. Synthesis of Zn(II) Schiff Base Complexes without
Substituent 43
III. Synthesis of Ethynyl-Substituted Zn(II) Schiff
Base Complexes 46
IV. Synthesis of Trinuclear Palladium-Zinc Complexes 55
V. Synthesis of Other Alkynyl-Substituted Zn(II)
Schiff Base Complexes 60
VI. Synthesis of Alkyl-Substituted Zn(II) Schiff
Base Complexes 63
VII. Photophysical Properties of The Salicylaldehydes
and The Zinc Series Complexes 67
a. 5-Substituted Salicylaldehydes 67
b. Zn(II) Schiff Base Complexes without Substitutent 69
c. Ethynyl-Substituted Zn(II) Schiff Base Complexes 70
d. Trinuclear Palladium—Zinc Schiff Base Complexes 73
e. Other Alkynyl-Substituted Zn(II) Schiff Base Complexes 74
f. Alkyl-Substituted Zn(II) Schiff Base Complexes 77
VIII. Series of Ni(II) Schiff Base complexes 80
Experimental 87
References 116
Chapter 3 Synthesis of Novel Multinuclear Polymeric and
Macromolecular Complexes Bridged By Pyridine
Diimine Ligand 124
Background 124
I. Tridentate NNN donor ligands 124
II. The 2,2’:6’,2”-Terpyridine Complexes 125
III. Bis(oxazolinyl)pyridine Complexes 127
IV. The 2,6-Bis(imino)pyridyl Complexes 129
Results and Discussion 135
I. Ethynylation of 2,6-Bis(imine)pyridine Ligand 135
II. Dipalladium and its Polym(yne) Complexes Bridging
with 2,6-Bis(imino)- pyridine Acetylene Ligand 138
III. Heterometallic Multinuclear Complexes 145
IV. Synthesis of Dipyridyl-Terminated 2,6-Bis(imino)-
pyridyl Ligand and its Polymerization Reaction
with Re(CO)5Br 152
Experimental 159
References 173
Concluding Remarks 179

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