2015 0717 retirement

國立台灣大學化學系特聘教授陳竹亭退休演講

July 17, 2015積學館松柏廳

https://www.facebook.com/jwuting.chenjtchen@ntu.edu.tw

A Career with Surprises of Anticipation

National Taiwan University

CHEMISTRY

羅銅壁

鄭玉瑕

楊寶旺

林隆清

林瑞槰

陳發清

林耀堂

劉盛烈

潘

貫

林渭川

楊昭華

許東明

辛淑琴

楊美惠

林敬二

張苕旭

劉廣定

陳立樹

https://en.wikipedia.org/wiki/Age_of_Enlightenment#/media/File:Salon_de_Madame_Geoffrin.jpg

Cultivation&

Enlightenment1965~1973

“There are some dead who are more alive than the living.” “No, no! It would be more true to say that there are some who are more dead than the dead.” “Maybe. In any case there are old things which are still young.”

Romain Rolland

羅曼．羅蘭貝多芬傳

Nobel Prize for Literature in 1915Stamp from the USSR which commemorates the 100th anniversary of Romain Rolland's birth in 1966

西方哲學西方教育西方音樂西方美術

威爾．杜蘭Will Durant, 1885-1981)

M.S. University of Cincinnati, Ohio 1975-1977

Ph.D. Iowa State University, Iowa, 1977-1982

傅斯年校長

NTU, B.S.1968-1973

CHEMICALRESEARCH

1986-2000Life is for Learning!

Organometallic Catalysis 有機金屬催化反應

Catalytic reactions 催化反應

Functional transformation 化學官能機轉換

Bond formation & cleavage 化學鍵形成與分解

Chemical Selectivity 化學選擇性

Structure & Structural isomerism 分子結構異構化

Synthesis 化學合成

Kinetics & Mechanism 動力學與反應機構

Catalytic Double Carbonylation

Penn State UJ. Am. Chem. Soc. 1984, 106, 1506-1507.J. Am. Chem. Soc. 1987, 109, 148-156.

Translocaion isomerism Acyl scrambling

黃倉淼Organometallics 1990, 9, 539-541.黃國良，黃倉淼Inorg. Chem. 1992, 31, 4034-4035.葉雨松Organometallics 1994, 13, 4804-4824.

All reactions are quantitative!!

黃倉淼J. Am. Chem. Soc. 1993, 115, 1170-1171.

M = Pt, Pd

Planar structure

δ+δ+

II

II

Synthesis of η3-allenyl/propargyl(C3H3)-Pt(II) Complex

Bond Formation and Functional Transformation

η3-oxatrimethylenemethane

η3-central carbonsubstituted allyl

η2-metallacyclobutatene

η3-azatrimethylenemethane

η3-trimethylenemethane

η3-terminalsubstituted allyl

η6-diallyl

蔡福裕， Organometallics 1997, 16, 822-823.Coord. Chem. Rev. 1999, 190-192, 1143-1168.

蘇崇智，J. Am. Chem. Soc. 1994, 116, 4999-5000.葉安琪，OMCOS10 Symposia-in-Print of Polyhedron, 2000, 19, 545-548."Platinum: Organometallic Chemistry" 2005 The Encyclopedia of Inorg. Chem., 2nd Ed., (EIC2), Weiley & Sons

The η3-allenyl/propargyl complexes are highly regioselectively electrophilic at the central carbon

and act as organometallic carbonium ions.

許瑞熙， J. Am. Chem. Soc. 1998, 120, 3243-3244.

Evidenced by D-labelling experiments.

intrinsic

INTERNATIONALACADEMY &

SERVICES 1999~2010

If there is something you know, communicate it. If there is something you don't know, search for it.

— An engraving from the 1772 edition of the Encyclopédie; Truth, in the top center, is surrounded by light and unveiled by the figures to the right, Philosophy and Reason.

NTU-RENNE U 1Exchange & Co-diploma Program

2003-2006

TRI-DEPARTMENT CHEMISTRY SYMPOSIUM

December 17, 2004

NTU-SNU-UT

NTU-Kanagawa UJoint Symposium on

Chemistry & Life ScienceAugust 25, 2006

Joint Symposium on Coordination Chemistry

August 25, 2006

NTU-Okayama U

Symposium on Commemoration of International exchange agreement

between NTU & OU (March 16, 2007)

Nationality No Nationality No Nationality No

Australia 6 Austria 3 Belgium 2Canada 25 Chile 4 China 28

Czech Republic 16 Denmark 1 France 32Germany 35 Hong Kong 9 Hungary 1

India 1 Iran 1 Israel 1Italy 6 Japan 151 Libya 1

Malaysia 2 Malta 1 Netherlands 7New Zealand 5 Poland 2 Portugal 5

Russia 21 Singapore 20 Slovenia 2South Africa 8 Korea 13 Spain 9Switzerland 12 Taiwan 253 Thailand 1

United Kingdom 36 United States 29

GENERAL EDUCATION

1995-2013

HIGH SCHOOL ED1992-beyond 2015

通識1995-1996 化學與生活1997-2004 從化學看世界2004-2009從科學與科技看人文社會議題

—科學人與社會人對話2010-2013 自然、環境與永續文明

物理是從萬象中究其一理，化學是從一理中尋其萬象環境問題的關鍵因是全球人口暴增。科技源自人性，卻未必有人文。為什麼一群聰明人會在一起做很笨的事？台灣究竟有百分之幾的笨蛋?社會有太多笨蛋顯然不是生物原因!先跑的不一定贏，現在贏的也不一定永遠贏。生命沒有悲觀的權利!

語錄

11:58:43 人類世 Anthropocene(0.00375秒)

如果將人類文明發跡的全新世(Holocene)，就是距今11,700年以內的時間視為24小時:

台灣第一本文本、中英文名詞索引、關鍵詞彙、每章重點等齊備的化學教科書。2000年發行

Why & How of Reading

閱讀是科學教育中不可取代的一種學習方法。教科書正是操演這種學習方法的最佳工具。閱讀教科書除了要理解書中的學科內容以外，也使讀者學習作者的思考方式與邏輯。一個會讀書的人，閱讀每一本書的主要目的正是要明白作者的思維方式與思想內容。基於這種教育理念，本書的撰寫……，冀能使潛心於閱讀的學子領悟有結構、有序理的知識，才會成為有用的學問。

6-12, Learning to Read, after 12, Reading to Learn!

CHEMICALRESEARCH2000-2015

Ligand Designfor unsymmetric Bidentate

李仁傑Dalton Trans. 2008, 5945-5956.

1

Ligand Design for unsymmetric Polydentate – A taste with bio-inorganic

2

N

P

N

Axialsite

Axialsite

monomer

Polymerchain

M

Geometric Isomerism in sqp Structure caused by Unsymmetric Bidentate Ligand Leading to Chemical Selectivity

1 σ-donor vs π-acceptor2 sp3-nitrogen vs sp2-nitrogen3 double substituents vs single substituent4 tetrahedral (109o) vs trigonal planar (120o)5 individual electronic/steric effect6 possibility for anionically charged or assymmetric ligand entity

Why unsymmetric imine-amine?

3

N N

楊豐兆，Dalton Trans. 2008, 5945-5956.

NiN

N BrBr

R2R2

R1 R1

Highly-branched PE

[Ni] =

• Catalyst (10 -12 mg) • MAO (10%, 6 mL) • 100 mL dried toluene• 250 psi ethylene• 25 ºC• Reaction quenched by HCl/MeOH• PE isolated by MeOH from toluene

• Mn = 105

• PDI < 2• Tg = -45~-50 ºC• TGA, stable until 390 ºC• 100~150 branches/1000 carbon• TOF = 105 g PE/mol Ni•h

General Features of products Reaction Conditions

AlO

Al

Me Me

MAO =n

H

H

H

H

[Ni]/MAO

4楊豐兆， Dalton Trans. 2009, 1243–1250

Isomers of Amine-Imine Complexes

+NR1R2

R3N(COD)PdMeCl

Pd

Cl

Me

R3

N

N

R1 R2

Pd

Me

Cl

R3

N

N

R1 R2

trans cis

25 oC

R1 = R2 = Et R3 = iPr 100 : 0R1 = R2 = Me R3 = iPr 85 : 15

R1 = R2 = Et, R3 = tBuR1 = R2 = c-C4H8, R3 = tBuR1 = R2 = Me, R3 = tBuR1 = H R2 = tBu, R3 = tBu

70 : 30 33 : 67

15 : 85 10 : 90

NN

NN

H

Note: The ligand does control geometric isomerism.7楊豐兆，Inorg. Chem. 2009, 48, 7639–7644.

Catalyst (60 μmol) 50 mL dried CH2Cl2 300 psi ethylene, 1~10 g norbornene 25 ºC, 30 min Reaction quenched by HCl/MeOH

Mw = 103~4

single modal Tg = 77~160 ºC TOF = 104 g / mol (Pd) • h NB % = 42~60 Alternating % = 76~94

General Features of products Typical Reaction Conditions

Cyclic Olefin Copolymer (COC)

Cationic

[Pd] =

林雅琪，Dalton Trans. 2009, 9058–9067.

Kinetics & Mechanism of MePd(II) Catalyzed E-N Copolymerization

18.7(15.1)

13.8(14.1)

17.6

14.0

19.6

19.6

19.6

kEE:17.3(17.6)

游國軒，unpublished.

CO2-abstraction induced by N8O2-Dicopper(II)

何宜學，Dalton Trans., 2014, 43 (17), 6287 - 6290.

JTC LAB ALUMNI

Acknowledgements M.S.Ms. Liu, C.-Y. 劉昭吟 Mr. Yeh, J.-L. 葉家良Mr. You, Y.-J. 尤彥傑 Ms.Chang, Y.-C. 張雅君Mr. Tseng, W.-H. 曾文華 Mr. Tsai, J.-C. 蔡嘉慶Mr. Hsu, B.-C. 許博治 Ms. Chen, Y.-C. 陳宜君Mr. Huang, G.-L. 黃國良 Mr. Yang, C.-T. 楊志璁Mr. Shi, H.-Y. 施皇宇 Mr. Wang, C.-C. 王哲峻Mr. Su, C.-C. 蘇崇智 Ms. Do, C.-C. 杜佳純Mr. You, B.-Y. 游本義 Mr. Wang, Y.-H. 王育恆Mr. Chen, Y.-K.陳玉堃 Mr. Chang, M.-J. 張慕傑Ms. Chen, A.-J. 陳藹然 Ms. Lin, H.-W. 林欣微Mr. Chen, H.-W. 陳鴻文 Mr. Liu, F.-Y. 劉豐瑜Mr. Cheng, Y.-C. 鄭原忠 Ms. Yu, H.-J. 游蕙如Mr. Chiang, W.-C. 江文智 Ms. Chang, C.-L. 張家綾Mr. Yu, C.-I. 余昭穎 Mr. Kuo, Tai- Heng 郭泰亨Mr. Chang, R.-T. 張瑞庭 Mr. Lin, Jia-Jheng 林佳正Ms. Tzeng, W.-T. 曾琬婷 Ms. Yu, Chi-Ying 余祈瑩

Ph.D.Dr. Yeh, Yu-Sung 葉雨松

Dr. Huang, Tsang-Miao 黃倉淼

Dr. Yang, Ching-Shuen 楊慶順

Dr. Tsai, Fu-Yu 蔡福裕

Dr. Hsu, Rai-Hsi 許瑞熙

Dr. Yeh, An-Chi 葉安祺

Dr Lee, Jen-Jeh 李仁傑

Dr Chu, Jan-Bon 朱建邦

Dr. Yang, Feng-Zhao 楊豐兆

Dr. Lin, Ya-Chi 林雅淇

Dr. Li Horng-Yi 李虹儀

Dr. Guan, Shih-Hau 管仕豪

Dr. Lin, Ya-Fan 林雅凡

Dr. Chang, I-Hsin 張益信

Dr. Yu, Kuo-Hsuan 游國軒Dr. Ho, Yi-Hsueh 何宜學

Dr. L. N. Patkar (postdoc)

Financial SupportNational Science Council (NSC) 國家科學委員會

The Netherlands Organisation for Scientific Research (NWO)

Crystallography & Calculation

Prof. Wang, Yu 王瑜

Prof. Peng, Shie-Ming 彭旭明

Prof. Jin, Bi-Yaw 金必耀

Assoc. Prof. Cheng, Yuan-Chung 鄭原忠

37

SCIENCE & EDUCATION

COMMUNICATION2007~2015

用任何創意或熱誠讓任何獨立、不相屬、不瞭解、不溝通、不對話、甚至不來往的社群互動連結就是在創造第三種文化。

網路、多媒體、創客都是第三種文化的契機，但是創造第三種文化的深層底蘊仍然是專業知識的品味。

感謝蒞臨