呂良賜 博士研究室 Research Interests:1. Green Technology

2. Novel Dye for Dye-sensitized Solar Cell

3. Synthetic Chemistry

4. Organometallic Chemistry

5. Fuel Cell (PEM membrane); Fluoropolymer

6. Material Science

Vacuum line

Current Research Projects

1. Novel Dye w/ Fluorous Polytail (Solar Cell)

2. Catalysis (Organometallics)

3. Fuel Cells

4. X-Ray Crystal Growing (Catalysts)

Current Research Projects

5. Green Chemistry Fluorous Biphasic System (FBS) Aerobic Alcohol Oxidation under FBS ATRP (Recoverable)

6. Lithium Battery Polymeric Electrolyte

1. Lithium Battery Electrolyte

See the next chart for the procedure

CF2I I6

+Na2S2O4 / NaHCO3

CF2NaO3S SO3Na6

+ Cl2

CF2ClO2S SO2Cl6

CF2FO2S SO2F6

metal fluoride+

+NH3

CF2H2NO2S SO2NH26

+ Li

CF2LiHNO2S SO2NHLi6

(A)

(B)

2. Liquid Crystal Materials

C5H11

C5H11

O

F F

F

F

F

1

F

F

F

2

Novel Fluorous Dye For DSSC Novel fluorous ponytailed Dye for Solar

Cell

CV and UV/VIS Studies of Pt-based DSSC

-0.8 -1.0 -1.2 -1.4 -1.6 -1.8 -2.0 -2.2-4.0x10-5

-2.0x10-5

0.0

2.0x10-5

4.0x10-5

6.0x10-5

8.0x10-5

Cu

rre

nt (

A)

Potential (V)

Pt complex 2a Pt complex 2b

Fuel Cell (Proton Exchange membrane)

Green Chemistry

1. FBS:Fluorous biphasic system

2. Aerobic Alcohol Oxidation under FBS

biphasic monophasic biphasic

3. ATRP (Cu recoverable)H2C C

CH3

C

OOCH3

Cu(I)/ Bipy

toluene

H2C C

CH3

C

OOCH3

BrCn

MMA mw 100bp:100 oC

H3C

CH3

COC2H5

O

反應完成聚合反應

進行

X-Ray

[4,4'-bis(C3F7CH2OCH2)-2,2'-bpy]

[4,4'-bis(HC4F8CH2OCH2)-2,2'-bpy]

Departmental Seminar on May 18 Host Speaker: Prof. Thrasher

Attending International Meeting in Yokohama, Japan (2007)

Photo with Nobel Prize Winner, Prof. Grubbs

Publication [A. 期刊論文 ( 以北科大發表之英文期刊 ; >10

papers)]

1. Norman Lu,* His-Chun Hou, Chien-Ting Lin, Yuh-Sheng Wen, and Ling-Kang Liu, “Synthesis, Structure and Electrochemical Property of Novel (2,2′-Bipyridine)-Metal (M = Pt, Pd) Dichloride with 4,4′-Bis(fluorous-ponytail) on Bipyridine” Eur. J. Inorg. Chem. 2009. (to be submitted) (NSC 96-2113-M-027-004-MY2)

2. Y. Akiyama, S. Fujita, X. Meng, Y.-C. Chen, N. Lu,b,* F. Zhaoc and M. Arai a,*, “Carbon Dioxide Pressure Tunable Heterogeneous and Homogeneous Media for Heck and Sonogashira Coupling Reactions Using Fluorinated Palladium Complex Catalysts” J. Organomet. Chem. 2009 (submitted) (NSC 96-2113-M-027-004-MY2)

3. Norman Lu,* and Ling-Kang Liu, J.C. Jiang “The Intramolecular Blue-shifting C-H···F-C Hydrogen Bond in Solid State”, CrystEngComm 2009 (submitted) (NSC 96-2113-M-027-004-MY2)

4. Norman Lu,a,* Yi-Chuan Chen,a Wei-Shung Chen, Ter-Lin Chen, Sy-Juen Wu “Copper-free Sonogashira Reaction under Thermomorphic Mode”, 2009, J. Organomet. Chem. (on-line release 2008, 10, 31), 694 (2), 278-284 (NSC 96-2113-M-027-004-MY2)(SCI:2.168, 12/43)

5. Norman Lu,* Tsung-Chi Chen and Ching-Lung Lin, “New Fluorous Bipyridine Ligands for Cu-catalyzed Atom Transfer Radical Polymerization of Methyl Methacrylate in the Thermomorphic Mode” J. of Applied Polymer Science, 2008, 110 (5), 2531-3303; (NSC 96-2113-M-027-004-MY2)(SCI: 1.008, 39/74)

6. Norman Lu,*, Shih-Chieh Chen, Tsung-Chi Chen and Ling-Kang Liu, “Pd-catalyzed Heck Reaction under Thermomorphic Mode” Tetrahedron Letters 2008, 49, 371-375; (NSC 96-2113-M-027-004-MY2), (SCI:2.615, 20/56)

7. Norman Lu,* Yan-Chou Lin, "High Fluorine Content Bis(fluoro-ponytailed) Bipyridine Palladium Complexes as Catalyst for Mizoroki-Heck Reactions under Fluorous Biphasic Catalysis Conditions" J. Chin. Chem. Soc. 2008, 55(1), 89-96; (NSC 95-2113-M-027-002), (SCI: 0.643, 91/128)

8. Norman Lu,* Yan-Chou Lin, “Efficient, Recoverable, Copper-catalyzed Aerobic Oxidation of Alcohols under FBS and Thermomorphic Mode” Tetrahedron Lett 2007, 48, 8823-8828; (NSC 95-2113-M-027-002) (96-2113-M-027-004-MY2) (SCI: 2.615, 20/56)

9. Norman Lu,* Jeng-Yung Chen, Chi-Wen Fan, Yan-Chou Lin, Yuh-Sheng Wen, and Ling-Kang Liu; “Synthesis, Structure and Reactivity of Novel Palladiumdichloride-2,2′-bipyridine with 4,4’-Bis(fluorous-ponytail)” Polyhedron 2007, 26, 3045-3053; (NSC 93-2113-M-027-005) (SCI:1.756, 10/25)

10. Norman Lu,* Yu-Mei Ho, Chi-Wen Fan, Fu-Ming Wang and Jyh-Tsung Lee,* “A Simple Method for Synthesizing Polymeric Lithium Salts Exhibiting Relatively High Cationic Transference Number for Solid Polymer Electrolytes” Solid State Ionics 2007, 178, 347-353; (NSC 93-2113-M-027-005) & (NSC 94-2113-M-027-003)(SCI:2.012, 12/61)

(Continued) 11. Norman Lu,* Yan-Chou Lin, Jeng-Yung Chen, Chi-Wen Fan, and Ling-Kang Liu;“ New Bis(fluoro-ponytailed)

Bipyridine Ligands for Pd-catalyzed Heck Reactions under Fluorous Biphasic Catalysis Condition” Tetrahedron 2007, 63, 2019-2023, NSC 94-2113-M-027-003, (SCI:2.869, 14/56)

12. Norman Lu(呂良賜 ),* Yan-Chou Lin(林原週 ), Jeng-Yung Chen(陳政湧 ), Chi-Wen Fan (范己文 ), Yuh-Sheng Wen(聞昱生 ), and Ling-Kang Liu(劉陵 崗 )* “(2,2’-bipyridine)palladium dichloride Derivatives as Recyclable Catalysts in Heck Reactions” J. Chin. Chem. Soc. 2006, 53, 1517-1521. NSC 94-2113-M-027-003,

(SCI: 0.643, 91/128) 13. Norman Lu,* H. P. Sampath Kumar, James L. Fye, Jian Sun Blanks, Joseph S. Thrasher, * Helge Willner, and Heinz

Oberhammer” The Initial Synthesis of the Long Sought After Compound Pentafluoronitrosulfane, SF5NO2” Angew. Chem. Int. Ed. 2006, 45, 938; rated as very important paper. NSC 94-2113-M-027-003, (SCI:10.031, 4/128)

B. Using other affiliation to publish 14. Norman Lu,* Joseph S. Thrasher, Stefan von Ahsen, Helge Willner,* Drahomir Hnyk, and Heinz

Oberhammer*“Pentafluoronitrosulfane, SF5NO2” Inorganic Chem. 2006, 45, 1783 (SCI:4.123, 4/43)

15. Howell*, J. L., Lu, N, Friesen, C. M. “New Derivatives of poly-Hexafluoropropylene Oxide from the Corresponding Alcohol”; J. Fluorine Chem. 2005.126, 281-288 (SCI: 1.513, 20/43)

16. Howell*, J. L., Lu, N.; Perez, E. W.; Howell, J. L.; Friesen C. M.; Novak, I.; Waterfeld, A.; Thrasher, J. S., “The Preparation of Primary Poly-Hexafluoropropylene Oxide Halides (Poly-HFPO-CF2X where X = I, Br, Cl and F)” J. Fluorine Chem. 2004.125,1513-1518 (SCI: 1.513)

17. DesMarteau, D. D., Lu, N., Zimmerman* P., Miller* D.; “Polymers Based on a Novel 1,3-perfluorodioxole for Use as a Soft Polymer Pellicle in 157nm Lithography” J. of Photopolymer Science and Technology, 2004,vol. 17, 651-654. (SCI: 0.835 ; 43/74)

 

International Meeting 1. “Fluorous Catalysis of Pd-catalyzed Heck Reaction under Thermomorphic Condition

without Fluorous Solvents: Facile Liquid/Solid Pd Catalyst Separation at RT" The 2nd International Symposium on Fluorous Technologies (ISoFT07), Yokohama, Japan, July 29-Aug.1, 2007. (oral); (NSC 95-2113-M-027-002)

2. “High Fluorine Content Bis(fluoro-ponytailed) Bipyridine Ligands for Pd-catalyzed Mizoroki-Heck Reactions under Fluorous Biphasic Catalysis Conditions” The 2nd International Symposium on Fluorous Technologies (ISoFT07), Yokohama, Japan, July 29-Aug.1, 2007. (poster); (NSC 95-2113-M-027-002)

“The study of using novel Cu complexes with fluoro-ponytailed bipyridine for the ATRP under thermomorphic mode” The 2nd International Symposium on Fluorous Technologies (ISoFT07), Yokohama, Japan, July 29-Aug.1, 2007. (poster); (NSC 95-2113-M-027-002)

4. “New Bis(fluoro-ponytailed) Bipyridine Ligands for the Pd-catalyzed Heck-type Reactions under Fluorous Biphasic and Thermophoric Conditions” The 2nd International Symposium on Fluorous Technologies (ISoFT07), Yokohama, Japan, July 29-Aug.1, 2007 (poster); (NSC 95-2113-M-027-002)

5. “Copper-catalyzed aerobic oxidation of alcohol under FBS and thermomorphic system” The 2nd International Symposium on Fluorous Technologies (ISoFT07), Yokohama, Japan, July 29-Aug.1, 2007. (poster); (NSC 95-2113-M-027-002)

6. “New Bis(fluoro-ponytailed) Bipyridine Ligands for the Pd-catalyzed Heck Reactions under Fluorous Biphasic Catalysis Condition” The 18th Winter Fluorine Conference (oral), St. Pete, FL, USA, Jan 14-20, 2007 (NSC 95-2113-M-027-002)

7. “New Bis(fluoro-ponytailed) Bipyridine Ligands for the Cu‑catalyzed Aerobic Oxidation of Alcohols under Homogeneous or Fluorous Biphasic System” The 18th Winter Fluorine Conference (poster), St. Pete, FL, USA, Jan 14-20, 2007 (NSC 95-2113-M-027-002)

8. ‘Synthesis, Structure and Reactivity of PdCl2[4,4'-Bis-RfCH2OCH2-2,2'-bpy] (Rf= C3F7, HC4F8, HC8F16 and C10F21)” The 18th ISFC- International Symposium on Fluorine Chemistry (Bremen, Germany, July 30- Aug.4, 2006) 國科會計 畫編號 NSC 94-2113-M-027-003

9. “Using α,ω-Perfluoroalkane Bis-sulfonyl Fluorides (FSO2C4F8SO2F, FSO2C6F12SO2F) as monomers And The Application of Their

Condensation Polymers For Solid Lithium Battery Electrolyte” the 17th International Symposium on Fluorine Chemistry (July 24-29, 2005) 國科會計畫編號 NSC

93-2113-M-027-005 10. Deparmental Seminar “Two Industrial Applications of Fluoropolymers:

Perfluoropolyalkylethers annd Lithium Battery Electrolytes” Univ. of Alabama, USA, Feb. 1, 2005.

歷年參與之研究計畫計劃名稱 起迄年月 委託機構

98-100年度國科會計畫 (合成新型含氟鏈聯吡啶及研究其應用在：一.陽離子型鈀錯合物催化，二.高穩定性及撥水之敏化太陽能電池，三.藍位移氫鍵)

98.8.1-100.7.31 國科會

96-97 年度國科會計畫 (一系列新奇之含氟鏈聯口比啶之合成；及以其為螯合劑所形成之鈀 ,銅及其他金屬錯合物之催化研究 ) (NT$2,655,000-2007-8; NSC 96-2113-M-027-004-MY2);

96.8.1-98.7.31 國科會

96年度國科會產學合作計畫:矽膠及相關產品之研究: 1.矽膠高分子樹脂之去除劑 2.使用超臨界二氧化碳回收矽膠 3. 水溶性矽膠介面接著劑之開發 (NT$ 459,550-2008)

96.11.1-97.10.31

國科會

特殊含氟化合物之合成及其在鋰電池，燃料電池及離子液體(ionic liquids)之應用 ( 2/2 NT$ 1,080,000-2006) (國科會計畫編號 NSC 95-2113-M-027-002;

95.8.1-96.7.31 國科會

產學合作計畫 (計畫名稱: 界面活性在高分子樹脂之應用研究 ) (NT$ 581,000) 94.11-95.10 國科會

特殊含氟化合物之合成及其在鋰電池，燃料電池及離子液體(ionic liquids)之用

(1/2 NT$ 1,113,000-2005) (國科會計畫編號 NSC 94-2113-M-027-003;

94.8.1-95.7.31 國科會

高分子鋰電池含氟素電解質聚合物之研製研究(國科會計畫編號 NSC

93-2113-M-027-005; NT $1,007,600)

93.8.1-94.7.31 國科會

註: 1. 皆為主要執行人; 2. 大約每年兩件研究計畫

3. 連續五年國科會一般計畫金額超過一百萬元 (總金額 7,486,150)

榮譽獎項及其他 榮獲國立台北科技大學工程學院 97 年度優等研究獎。 2007.8 升副教授。 指導研究生學生林原週、陳宗琦及陳世傑投稿國際會議

(The 2nd International Symposium of Fluorous Technology; ISoFT ) 被接受；且每位學生獲得國科會 3 萬元之補助，去參與會議。

Invitation You are cordially invited to join this group

for the cutting-edge research.