Synthesis, Characterization and Catalytic
Application of Aminodipyridylphosphine Oxide
Copper(II) Complex and Its Supported Form on
Gold Nanoparticles
學生 : 曹嘉榮
指導老師 : 于淑君 博士
HO
3
N
H
O
P
N
N
Cu
OTf
OTf
Annulation Reactions of ArOH with 1,3-Dienes
R
O
(OTf)2Cu(2-py)2 P N
H
O
(OTf)2Cu(2-py)2 P N
H O
N P(2-py)2Cu(OTf)2
SS S
S Au S
SSS
H
10
Catalyst 5 mol %
+
OH
CH2Cl2, 50oC, 18 h
R
O
H O
N P (2-py)2Cu(OTf)2
1
Phosphine Ligand
 Phosphines are electronically and sterically tunable.
P
O
P(Bu)3
P O
O
P(OiPr)3
P
P
P(Me)3
P(o-tolyl)3
 Drawbacks and Limitations
 Expensive.
Triphenylphosphine $20.3 USD(1g) ReagentPlus®,99% (Sigma-Aldrich)
 Chemical waste.
 Air and thermal instability.
H
O2
PPh2
C
O
 a. Oxidation
O
N
N
(EtO)3Si
O
O
O Si
H
N
PPh2
C
Oxidation
PPh2
OEt
 b. Metal Leaching
H
N
N
(EtO)3Si
N
PPh2
C
O2
Metal Leaching
O
PPh2
RhL2
OEt
O
O Si
P
Ph2
H
N
O
O
N
PPh2
C
O
O
+
RhL2
PPh2
To develop bipyridne lignad to replace phosphine ligand is necessary.
2
Kinzel, E. J. Chem. Soc. Chem. Commun. 1986 1098.
Hybrid Catalysts
Concepts:
1. Increasing the Heterogeniety of the Homogeneous Catalyst Systems
2. Combining the Both Benefits of Homogeneous and Heterogeneous Systems
= Molecular Metal Complex Catalyst
= Spacer Linker
A
A
= Anchoring Group
= Metal or Metal Oxide Surface
3
Types of Catalysts
Characteristics of
catalysts
Cat. structure
Homogenous Heterogeneous
Hybrid
Known
Unknown
Known
Catalyst modification
Easy
Difficult
Easy
Activity
High
Low
High
Selectivity
High
Low
High
Conditions of catalysis
Mild
Harsh
Mild
High risk
Low risk
Low risk
Mechanical strength
Low
High
High
Cat. stabilities
Low
High
High
Separation ＆ recycle of cat.
Difficult
Easy
Easy
Industrialization
Difficult
Applicable
Applicable
Poisoning of cat.
4
Bulk-Surface
I. Metal Oxide :
(SiO2), (Al2O3), (zeolite), MCM-41, ..etc.
II. Silical gel
III. Organic polymer :
Polystyrene (PS), Organic Dendrimers
IV. Nano particles:
5
Metal Oxide-Supported Catalysts
Piaggio, P.; McMorn, P.; Murphy, D.; Bethell, D.; Page, P. C. B.; Hancock, F. E.; Sly, C.; Kerton, O. J.
; Hutchings, G. J. J. Chem. Soc., Perkin Trans. 2 , 2000, 2008-2015.
6
Polystyrene-Supported Catalysts
7
Chem. Rev. 2002, 102, 3275-3300.
Silica-Supported Catalysts
8
Chem. Rev. 2002, 102, 3495-3524.
Nanoparticles-Supported Catalysts
Ru catalyst for ringopening metathesis
polymerization (ROMP) to gold colloids.
Tremel. W. Angew. Chem. Int. Ed. 1998, 37, 2466-2568.
Pfaltz, A. J. Am. Chem. Soc. 2005, 127, 8720-8731.
9
Catalyst Design
catalyst
Au NPs
with controllable solubility
Au NPs have been known not only to
possess solid surfaces resembling the
(1 1 1) surface of bulk gold but also to
behave like soluble molecules for their
dissolvability,
precipitability,
and
redissolvability.
soluble metal complex
functional groups
coordinationl ligands
spacer linker
10
Lin, Y.-Y; Tsai, S.-C.; Yu, S. J. J. Org. Chem. 2008, 73, 4920-4928.
The Catalytic Applications of Cu(II)
Goldberg reaction
Ullmann, F.; Bielecki, J. Iram Goldberg, Chem. Ber. 1901, 34, 2174.
 Diels-Alder Reactions
C-O Bond Formation
 Friedel-Crafts Alkylation Reactions
C-C Bond Formation
 O-arylation of Phenols
Asymmetric Arylation of Imines
 Oxidation of Alcohols
Oxa-Diels-Alder Reaction
 Enantioselective Diels-Alder Reaction Thia-Diels-Alder Reaction
 Enantioselective Friedel-Crafts Reaction
 Asymmetric Addition of Dialkylzinc to Imines

11
Drawbacks of Traditional
Copper-mediated Reactions
 Insoluble in organic solvents
- heterogeneous
- needed large amount catalyst
 Harsh reaction conditions
- high temperatures around 200 °C
- strong bases
- toxic solvent such as HMPA
- sensitive to functional groups on aryl halides
- long reaction times
- the yields are often irreproducible

The catalyst sructure is not well defined
12
Annulation of Phenol Derivatives with 1,3Dienes to Construct The Chroman Structure
Conventional Lewis Acids and Transition Metal Lewis Acids
BF3-Et2O、ZnCl2、AlCl3、SnCl4、 Sb(OTf)3、 Sc(OTf)3、 Y(OTf)3
M. Matsui and H. Yamamoto, Bull.Chem.Soc.Jpn. 1995, 68, 2657-2661.
M. Matsui and H. Yamamoto, Bull.Chem.Soc.Jpn. 1995, 68, 2663-2668.
Conventional Bronsted Acids
Chroman skeleton
H3PO4、H2SO4 、Zeolite HSZ-360
Vitamin E
V. K. Ahluwalia and K. K. Arora, J. Chem. Soc., Perkin Trans.1, 1982, 335.
F. Bigi, S. Carloni, R. Maggi, C. Muchetti, M. Rastelli and G. Sartori, Synthesis, 1998, 301-304.
G. P. Kalena, A. Jain and A. Banerji, Molecules, 1997, 2, 100-105.
Drawbacks of these acid promoted processes
1、High reaction temperatures are often necessary!
2、In most cases, only low to moderate yields of products were reported.
13
Construction of The Chroman Structure by
Annulation Reactions of ArOH with 1,3-Dienes.
R. V. Nguyen, X. Q. Yao and C. J. Li, Org. Lett., 2006, 8, 2397- 2399.
S. W. Youn and J. I. Eom, J. Org. Chem., 2006, 71, 6705- 6707.
Cat. CpMoCl(CO)3
5 mol %
Yamamoto, H. and Itonaga , K , Org. Lett., 2009, 11 , 717–720.
14
Motivation
 Copper is less expensive than other transition metals.
- PdCl2
-NiCl2
- Cu(OTf)2
$269.5 USD(5g) ReagentPlus® (Aldrich)
$139 USD(5g) reagent grade (Sigma-Aldrich)
$64.7 USD(5g) reagent grade (Sigma-Aldrich)
 Using bipyridine ligand to replace phosphine ligand in
organomatallic catalysis.
 To study the immobilization of molecular copper(II) complexes
on the surfaces of Au NPs by using the covalent linkage via a
specially designed bipyridine ligand as spacer linkers.
 Catalysis under efficient microwave flash heating to replace
conventional thermal heating.
 Easily recovered and effectively recycled copper(II) complexs
immobilized onto Au Nanoparticles.
15
Preparation of Aminodipyridylphosphine
Oxide Ligand
1.NaN3 / DMF
Br
OH
2. RT / 6 hour
N3
1
N3
+
N
93 %
Dry CH3CN 60 ml
P
HO
OH
N
reflux 16 hr
N
Staudinger
[P(2-py)3]
HO
N
P
N
N
HO
N
Iminodipyridylphosphorane Ligand
1ml DI water
2
75 %
N
H
O
P
N
N
Aminodipyridylphosphine Oxide Ligand
Lin, Y.-Y; Tsai, S.-C.; Yu, S. J. J. Org. Chem. 2008, 73, 4920-4928.
16
Synthesis Copper(II) Complex Catalyst
Cu(OTf)2 = Cu2+ (CF3SO3-)2
HO
N
H
2
O
P
N
N
Cu(OTf)2
Mix solvent CH2Cl2:CH3CN= 5:1, RT, 12 hr
HO
3
80%
N
H
O
P
N
N
Cu
OTf
OTf
Cat.
Elemental Analysis：
Anal. Calcd for C23H32CuF6N3O8PS2 (750.06)：C, 36.78; H, 4.29; N, 5.59.
Found：C, 36.92; H, 4.36; N, 5.11.
IR (KBr) :
ν
C
C, C
N
Ring stretching = 1592(s), 1437 (s)
17
Synthesis of Spacer-Linker
Br
NaN3 / DMF
OH
N3
OH
rt / 6hr
4
97 %
1. CS(NH2)2 / ethanol
PBr3 / ether
N3
2. reflux , 16 hr
Br
3. NaOH / 5 min
rt / 6hr
5
4. HCl /20 min
55 %
P(2-py)3
HS
N3
H2O / CH3CN
O
N P
H
HS
110 oC / 16 h
6
50 %
N
N
7
75 %
Lin, Y.-Y; Tsai, S.-C.; Yu, S. J. J. Org. Chem. 2008, 73, 4920-4928.
18
Synthesis of the RS-Au-L-Cu(OTf)2 (10)
1. [CH3(CH2)7]4N+Br-/CHCl3/rt/1h
2. CH3(CH2)7SH/CHCl3
3. NaBH4/H2O/12h
HAuCl4. 4H2O
H O
HS(CH2)11N P(2-py)2
SSS
S Au S
SSS
CHCl3, 80oC,16 h
8
HO
N P(2-py)2
O
(2-py)2P N
H
O
(2-py)2P N
H
SS S
S Au S
SSS
9
O
N P(2-py)2
H
O
(OTf)2Cu(2-py)2 P N
H
Cu(OTf)2 / dry CHCl3:CH3CN = 6 :1
rt / 16 hr
O
(OTf)2Cu(2-py)2 P N
H
H O
N P(2-py)2Cu(OTf)2
SS S
S Au S
SSS
H O
N P (2-py)2Cu(OTf)2
10
19
IR Spectra of Ligand (2), and Complex (3)
20
FAB-MS Spectrum of
[HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2 (3)
｛[HO(CH2)11N(H)P(O)(2-py)2]Cu}+ = 452 (m/z) ｛[HO(CH2)11N(H)P(O)(2-py)2]CuOTf}+ = 601 (m/z)
120.0
100.0
Simulated MS Data
[M – 2OTf]+
110.0
452.16
100.0
90.0
Simulated MS Data
[M – OTf]+
90.0
80.0
70.0
80.0
70.0
60.0
60.0
50.0
50.0
454.16
601.21
603.11
40.0
40.0
30.0
30.0
453.16
604.11
455.16
10.0
0.0
451.00
451.50
452.00
452.50
453.00
453.50
602.11
20.0
20.0
454.00
454.50
455.00
455.50
10.0
456.00
456.50
457.00
0.0
600.00
601.00
602.00
603.00
Experimental MS Data
HO
N
H
2OTf
N
N
Cu
605.00
606.00
607.00
Experimental MS Data
[M – OTf]+
[M – 2OTf]+
O
P
604.00
HO
N
H
O
P
OTf
N
N
Cu
OTf
21
Single-Crystal X-ray Structure of
[CH3(CH2)3N(H)P(O)(2-py)2]Cu(OTf)2 (13)
N
H
Bond lengths [Å] and Bond angles [deg]
Cu(1)-N(1)
Cu(1)-N(2)
Cu(1)-O(4)
N(1)-Cu(1)-N(2)
N(1)-Cu(1)-O(4)
N(2)-Cu(1)-O(4)
1.998
2.020
2.325
90.06
93.48
96.16
O
P
N
N
CH3CN
Cu
H2O
OTf
OTf
Empirical formula C18 H23 Cu F6 N4 O8 P S2
Temperature
100(2) K
Space group
P -1
Unit cell dimensions
a = 26.022(2) Å
α = 90°.
b = 13.5072(11) Å
β = 117.2320°.
c = 17.0090(14) Å
γ = 90°.
Volume 5315.8(7) Å3
Final R indices [I>2sigma(I)]
R1 = 0.0410, wR2 = 0.0841
22
1
H NMR Spectra of Au NPs (9) and (10)
RS-Au-L(9)
O
(2-py)2P N
H
O
(2-py)2P N
H
HO
N P(2-py)2
SS S
S Au S
SSS
O
N P(2-py)2
H
-HNCH2-
9
RS-Au-L
H2O
d6-DMSO
＃
＊
＃
＊
Py
NH
RS-Au-L-Cu(OTf)2(10)
H O
N P(2-py)2Cu(OTf)2
O
(OTf)2Cu(2-py)2 P N
H
O
(OTf)2Cu(2-py)2 P N
SS S
S Au S
SSS
H O
N P (2-py)2Cu(OTf)2
H
10
23
XPS Data of RS-Au-L-Cu(OTf)2 (10)
4f5/2
4f7/2
87.6
83.9
11. {3,10-bis(3'-nitrobenzoyl)-4,9-dimethyl-5,8diazadodeca-4,8-diene-2,11-dionato}copper(II): N2O2.
Manabu FUJIWARAT, et al. , Analytical Sciences, 1993, 9 , 289-291
24
IR Spectra of Ligand (7),
Au Nanoparticles (9), (10) and Complex (3)
7
9
10
3
1425 cm-1
1435 cm-1
1437 cm-1
25
IR Spectra Region Enlargement of Ligand
(7), Au Nanoparticles (9), (10)
HS-(CH2)11NHP(O)(2-py)2 (7, L)
RS-Au-L (9)
RS-Au-L-Cu(OTf)2 (10)
3000
2500
-1
Wavenumber(cm )
26
TEM Image of Octanethiol Protected
Au-SR NPs(8)
HAuCl4 . 4H2O
+
-
CH3(CH2)7]4N Br
CHCl3
CH3(CH2)7SH /CHCl3
NaBH4 / H2O
S S S
S Au S
S SS
8
Particle size distribution 2.68 ± 0.3 nm
27
TEM Image of RS-Au-L (9)
HO
N P(2-py)2
O
(2-py)2P N
H
O
(2-py)2P N
H
SS S
S Au S
SSS
O
N P(2-py)2
H
9
Particle size distribution 3.1 ± 0.25 nm
28
TEM Image of RS-Au-L-Cu(OTf)2 (10)
O
(OTf)2Cu(2-py)2 P N
H
O
(OTf)2Cu(2-py)2 P N
H
H O
N P(2-py)2Cu(OTf)2
SS S
S Au S
SSS
H O
N P (2-py)2Cu(OTf)2
10
Particle size distribution 3.52 ± 1.2 nm
29
UV-vis Spectra of Ligand (7), and
Au Nanoparticles (8), (9) and (10)
4
HS(CH2)11N(H)P(O)(2-Py)2 7
Au-SR 8
RS-Au-L 9
RS-Au-L-Cu(OTf)2 10
257 nm
abs
3
2
517 nm
1
0
300
400
500
nm
600
700
800
30
EPR Spectra of Cu(II) Complex (3)
and RS-Au-L-Cu(OTf)2 (10)
HO
N
H
O
P
N
OTf
Cu
N
OTf
g∥=2.333
g⊥=2.082
3
g∥=2.331
g⊥=2.080
Evans, D. A .et al. J. Am. Chem. Soc. 1997, 119, 7893-7894.
H O
N P(2-py)2Cu(OTf)2
O
(OTf)2Cu(2-py)2 P N
H
O
(OTf)2Cu(2-py)2 P N
H
SS S
S Au S
SSS
H O
N P (2-py)2Cu(OTf)2
10
g∥=2.311
Anna M. Duda et al. J. Agric. Food Chem., 1996, 44 , 3698–3702 .
g⊥=2.074
S. Tanaka et al. Journal of Catalysis ,
2007, 245 ,173–183.
31
Reported Copper(II) Catalytic Annulation of
Phenols with 1,3-Dienes
Catalyst =
(5 mol%)
2+
Cu
(CF3SO3-)2
N
N
+
2,2'-bipyridine
Adrio, L. A.; Hii, K. K. Chem. Commun. 2008, 2325–2327
32
Cu(II) Complex 3-Catalyzed Annulation
Reactions of ArOH with 1,3-Dienes.
[HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2 (3)
R
+
OH
Entry
Phenol
Dienes
CH2Cl2, 50oC, 18 h
Yield(%)a
Entry
MeO
1
R
5 mol %
O
Phenol
Dienes
I
OH
80
6
OH
Yield(%)a
57
68b
Cl
2
OH
78
7
70
OH
3
OH
60
8
OH
4
85
9
63
72b
10
OH
Br
5
OH
OH
53
66b
95
94
OH
General reaction conditions: Phenol/ Naphthol (1 equiv.), Dienes (1.5 equiv.), Catalyst (0.05 equiv.)
Solvent = 0.2 mL, 50 oC, 18 h. a Yields were determined by NMR. b. Catalyst (10 mol %).
33
Cu(II) Complex 3-Catalyzed Annulation
Reactions of ArOH with 1,3-Dienes
[HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2 (3)
R
5 mol %
+
OH
Entry
11
Phenol
MeO
Dienes
CH2Cl2, 50oC, 18 h
Yield(%)a
72
Entry
16
O
Phenol
70
OH
14
17
OH
52
MeO
87
OH
65
18
72b
19
74c
20
OH
15
Yield(%)a
OH
OH
13
Dienes
Br
OH
12
R
OH
OH
OH
General reaction conditions: Phenol/ Naphthol (1 equiv.), Dienes (1.5 equiv.), Catalyst (0.05 equiv.)
Solvent = 0.2 mL, 50 oC, 18 h. a Yields were determined by NMR. b. Catalyst (10 mol %).c.Temperature 80 oC.
81
62
88
34
Proposed Mechanism of Annulation
Reactions of ArOH with 1,3-Dienes
OH
HO
N
H
OTf
O
P
N
N
Cu
N
N
OTf
OTf
OTf
N
N
Cu
+ HOTf
O
OTf
N
N
Cu
O
Cu
O
OTf
N
N
Cu
O
H
Claisen rearrangement
N
N
Cu
OTf
OTf
O
Product
35
Comparison of Catalytic Activity
between Cat. 3 and Cat. 10
R
Catalyst 5 mol %
+
OH
Entry
1
Phenol
Diene
MeO
R
CH2Cl2;CH3CN= 8 : 1 , 50oC, 18 h
O
Yield(%)a
Yield(%)a
[HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2 (3)
RS-Au-L-Cu(OTf)2 (10)
72
68
64
73
69
70
75
66
49
57
65
56
63
67
OH
MeO
2
OH
3
OH
4
OH
Br
5
OH
6
OH
7
OH
36
Thermal v.s. Microwave Heating
Microwave
Thermal
Convection transition
Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
37
Microwave Assisted Annulation Reactions of
ArOH with 1,3-Diene
R
5 mol % Catalyst
+
OH
Entry
1
Phenol
Diene
MeO
R
Microwave 600w
0.5 mL IL-Bmim-PF6
O
Yield(%)a
Yield(%)a
[HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2 (3)
RS-Au-L-Cu(OTf)2 (10)
69 (50s)
84 (50s)
72 (50s)
81 (50s)
78 (50s)
87 (50s)
66 (50s)
71 (50s)
70 (50s)
78 (50s)
71 (50s)
76 (50s)
72 (50s)
80 (50s)
OH
2
OH
3
OH
Br
4
OH
5
OH
6
OH
7
OH
General reaction conditions: Phenol/ Naphthol (1 equiv.), Dienes (1.5 equiv.), Catalyst (0.05 equiv.) a Yields were
determined by NMR.
38
Au NPs Conducting Microwave and Acting as
Hot Spot in Microwave Irradiating Process
Temperature
after
microwave
600 W
irradiating for
50 (sec)
Microwave
600 W
irradiating
Time required
to reach
temperature
120 oC
Room Temperature(22 oC)
Blank
0.5 mL IL-Bmim-PF6
[HO(CH2)11N(H)P(O)(2py)2]Cu(OTf)2 (3) + 0.5 mL
IL-Bmim-PF6
RS-Au-L-Cu(OTf)2 (10) + 0.5
mL IL-Bmim-PF6
Au Nps +
[HO(CH2)11N(H)P(O)(2py)2]Cu(OTf)2 (3) + 0.5 mL
IL-Bmim-PF6
23 oC
164 oC
171 oC
o
232 C
215 oC
Room Temperature(26 oC)
0.5 mL DMSO
360 (s)
[HO(CH2)11N(H)P(O)(2py)2]Cu(OTf)2 (3) + 0.5 mL
DMSO
250 (s)
RS-Au-L-Cu(OTf)2 (10) + 0.5
mL DMSO (homogeneous)
168 (s)
Au Nps +
[HO(CH2)11N(H)P(O)(2py)2]Cu(OTf)2 (3) + 0.5 mL
DMSO (heterogeneous)
191 (s)
39
(RS-Au-L) - (Ligand loading % )
Microwave 600w irradiating to reach temperature 120 oC
0.5 mL DMSO
Time (second)
+
Microwave
irradiating
350
300
250
200
150
100
50
0
315
0.037
185
160
110
0.075
0.113
0.151
Au (mmole)
Detection
Temperatre (oC)
Temperature after Microwave 600w irradiating for 120 (sec)
350
300
250
200
150
100
50
0
0.037
0.075
0.113
0.151
Au (mmole)
40
Recycling Tests on Cat. 10 for Annulation
Reactions of ArOH with 1,3-Dienes.
RS-Au-L-Cu(OTf)2 (10)
20 mol%
CH2Cl2;CH3CN= 10 : 1 , 50oC
Recycling
NO.
Time
(hr)
Conversion
(%)
1
3
99
2
3
96
3
3
96
4
3
96
5
3
95
6
3
96
7
3
94
8
3
97
9
3
10
3
11
3
O
100
Conversion(%)
+
OH
80
60
40
20
0
1
2
3
4
5
6
7
8
Recycling NO.
Filtrate showed no further reactivity
41
Conclusions
1.The air- and water-stable catalyst [HO(CH2)11N(H)P(O)(2-py)2]Cu(OTf)2
(3) was synthesized and characterized by IR, FAB-MS, EPR , XPS, X-ray,
EA.
2.We have developed a methodology to successfully immobilize molecular
Cu(II) complexes onto surfaces of Au NPs. The structure of the
supported Au NPs-S(CH2)11N(H)P(O)(2-py)2Cu(OTf)2 (10) catalyst was
characterized by 1H-NMR, IR, TEM, UV, XPS ,EPR , AA.
3.We have successfully demonstrated the catalytic activity of the Cu(II)
complex for the annulation reactions of ArOH with 1,3-dienes.
4.The successful use of microwave irradiation for the annulation reactions
of ArOH with 1,3-dienes to further accelerate reaction rates and to
improve conversions.
5.The Au NPs-Cu(II) catalyst (10) can be quantitatively recovered and
effectively reused for many times without significant loss of reactivity.
42
Standard calibration curve of copper(II)
standard solution
43
120.0
110.0
452.16
100.0
90.0
80.0
70.0
60.0
50.0
454.16
40.0
30.0
453.16
20.0
455.16
10.0
0.0
451.00
451.50
452.00
452.50
453.00
453.50
454.00
454.50
455.00
455.50
456.00
456.50
457.00
44
100.0
90.0
80.0
70.0
60.0
601.21
603.11
50.0
40.0
30.0
602.11
20.0
604.11
10.0
0.0
600.00
601.00
602.00
603.00
604.00
605.00
606.00
607.00
45
0.05 equiv catalyst
+
OH
MeO
OH
16 hr
52 %
67 %
12 hr
16 hr
54 %
71 %
18 hr(50 oC)
78%
o
0.2 mL CH2Cl2 ,80 C
O
0.05 equiv catalyst MeO
+
12 hr
0.2 mL CH2Cl2 ,80 oC
O
18 hr(50 oC)
80%
46
Time (second)
Microwave 600w irradiating to reach temperature 120 oC
350
300
250
200
150
100
50
0
315
185
160
110
0.037
0.074
0.111
0.148
Au (mmole)
Microwave 600w irradiating to reach temperature 120 oC
Time (second)
100
80
• 各種物質導熱係數
Material conductivity
diamond 鑽石
silver
銀
copper
銅
gold
金
aluminum 鋁
k (W/m·K)
2300
429
401
317
237
80
60
40
45
33
20
25
0
0.037
0.074
0.111
Cu (mmole)
0.148
47