1123生活化學

生活化學

Huan-Tsung Chang

Department of Chemistry

National Taiwan University

[email protected]

張煥宗

化學是一門研究物質的性質、組成、

結構、及變化規律的基礎自然科學。

化學研究的對象涉及物質之間的相互

關係，或物質和能量之間的關係。

例如

: 碳氫氧三種原子可結合成許多不同性質的化合物。

固體於水中的溶解度

?吸熱或放熱?

3

1.溶液的性質

2.酸(Acid)與鹼(Base)

3.沉澱反應

4.氧化還原反應

5.界面活性劑

6.感測器

7.綠色化學

生活中的化學

極性溶液

: Hydrophilic solvent

非極性溶液

: Hydrophobic solvent

萃取

: 濃縮和減少基質干擾

液相萃取

固相萃取

超流體萃取

微萃取光纖

減少溶液用量

加快萃取速度

CO

₂

超流體從

咖啡中萃取

咖啡因

7

酸: 解離

鹼

: 水解

隨著有機酸碳鏈增長，

那些性質會改變

?

CH

₃

COOH

CH

₃

CH

₂

COOH

CH

₃

(CH

₂

)

₄

COOH

CH

₃

(CH

₂

)

₁₀

COOH

CH

₃

(CH

₂

)

₁₆

COOH

9

碳鏈越長

:

水溶性越差

分子作用力增加

揮發性遞減

(固體性質增加)

如何增加油水互溶性

?

11

酸鹼指示劑

當土壤偏酸性pH值5至5.5以下

時，土壤中的金屬離子會與植物

13

Solubility product (K

): 溶解度越小，溶解度越差

沉澱反應

Ag

+

_{+ Cl}

-

_AgCl

Pb

2+

_{+ CrO}

4

2-

PbCrO

4

Fe

3+

_{+ 3(OH)}

-

_Fe(OH)

3

3Ca

2+

_+2PO

4

3-

Ca

3

(PO

4

)

2

沉澱的應用

?

氨水為何可除鐵鏽

?

15

Ag

₂

S

CdS

_HgS

砒霜

(白色霜狀粉末): 三氧化二砷，分子式

As O 。古時砒霜不純，常含有硫化物。

砒霜中

會混有大量的

硫

或

硫化物

，呈現紅色，故又稱

「鶴頂紅」

ZnS

氧化反應

: 失去電子的反應

19

防止鐵生鏽

?

隔絕空氣

避水

1. 在鐵製品表面覆蓋保護層如油漆等:

防鏽漆容易受

外在環境影響剝落。

2. 表面覆蓋比鐵更容易氧化的物質(如鋅和鎂):

把鋼材表面直

接「包膜」，裹上一層鋅，防鏽更持久。利用攝氏400~500度高溫把鋅溶成液態

，把鋼材浸入，冷卻後就成了鍍鋅防鏽膜。

3. 合金

防止鐵製品生鏽

鋼（

Steels): 鐵－碳合金，除了含有碳元素外，

亦可進一步包含微量其它合金元素。

低碳鋼

(C <0.25%)、中碳鋼(C <0.60%) 、高碳鐵(C <1.40%)

23

水果去皮後，果肉會直接接觸氧氣，在氧的作用下，

水果中含有的「兒茶酚等酚類」物質，會和另一種物

質「多酚氧化酶」，發生「酶促褐變反應」，形成

「黑色素」，也就是我們常說的水果變色。

泡水或鹽水

水果包上保鮮膜

添加天然還原劑

:滴幾滴富

含檸檬酸和維他命

C的果汁

將茶持續泡在水裡，茶葉裡的單寧酸、咖啡因會一直

釋出，使茶湯苦澀難入口，還有大量咖啡因，容易讓人心悸、胃不舒服。

pH 3.0 pH 8.0 pH 9.0 pH 10.0

Size effect

Large surface area

Nanomaterials-Gold and silver

還原劑常用於合成金屬奈米粒子

鹼性條件下，糖還原銅離子形成銅奈米粒子

酸性條件下，檸檬酸還原金離子形成金奈米粒子

於氨水中，甲醛和銀離子的反應

:

27

膠體

(colloid)和奈米粒子 (nanoparticles

奈米粒子

: 1-100 nm (10

-9

m)

HAuCl₄(aq) + Na₃C₆H₅O₇(aq) Au NPs + CO₂ + HCOOH + …

3-Mercaptopropionic acid

A. Negatively charged thiols

B. Neutral thiols

31

Preparation of 11-MUA-L

12 L tetrakis(hydroxymethyl)phosphonium chloride (THPC) in 46 mL DI water Add 0.5 N NaOH (1 mL) Au NPs 10 mM 11-mercaptoundecanoic acid (11-MUA) THPC 11-MUA 11-MUA-L_AuND 10 nm 1% hydrogen tetrachloroaurate(III) trihydrate (HAuCl₄·3H₂O) 1.5 mL

Au NP

Au

11-MUA-L

Angew. Chem. Int. Ed.

Au Au NP

Mannopyranoside grafting thiol

Au

Synthesis of Fluorescent

Carbohydrate-Protected Au Nanodots for Detection of

Concanavalin A and Escherichia coli

450 500 550 600 650 0

1.0 2.0

[E. Coli] (10

_cells/mL)

100.0 50.0 37.5 25.0 10.0 5.0 2.5 0

[E. Coli] (108 _cells/mL)

0 1.0 2.0 3.0 0 1.0 2.0

I

(a. u.)

Wavelength (nm)

I

(a. u.)

Glow stick contains two chemicals and a suitable

dye (sensitizer, or fluorophor).

is used in a luciferin-luciferase system

that requires ATP as a cofactor. the most "popular" of the marine luciferins. This molecule can occur in

luciferin-luciferase systems, and is famous for being the light emitter of the photoprotein

"aequorin".

Firefly luciferin

Coelenterazine

0.6 picograms of adenosine triphosphate (ATP) or 0.1 femtograms of luciferase

Photuris pennsylvanica was measured to be 552 nm (green-yellow)

37

臨界微胞濃度（

Critical micelle

A micelle

is an aggregate of surfactant molecules dispersed in a

liquid colloid. In aqueous solution, aggregates are formed with the

hydrophilic "head" regions in contact with surrounding solvent,

sequestering the hydrophobic single-tail regions in the micelle center.

This type of micelle is known as a normal-phase micelle

(oil-in-water micelle) as shown in (a). Inverse micelles have the head

groups at the center with the tails extending out (water-in-oil micelle)

as shown in (b).

39

冰塊＋鹽水

鮮奶油 和 芒果泥混合均勻，然後加入

一顆蛋黃

(卵磷脂；乳化劑)

41

感測器

(Sensor)

偵測器

訊號傳輸

感應端

Fiber-optic sensors are good alternatives to electrodes, with

no requirement for a reference electrode.

Fluorescence

ELISA: enzyme-linked

immunosorbent assay

45

攝護腺特異抗原

(Prostate Specific

Antigen; PSA): 在攝護腺肥大的病

人也可能昇高。

癌胚抗原

(carcinoembryonic antigen，

CEA; CEA): 大腸直腸癌的病人才會增加，

在乳癌、肺癌、胃癌等很多癌症都可能會

增高，而且在肝硬化、肺病變、抽菸等情

形也會增加。

胎兒球蛋白（

alpha-fetoprotein; AFP）: 肝

癌病人可能昇高。

ELISA檢測癌症標記物:

綠色化學的基本精神

低毒

低能

高效率

再生

P T Anastas and J C Warner (1998):

Green chemistry is the utilization of a set

of principles that reduces or eliminates

the use or generation of hazardous

substances in the design, manufacture

and application of chemical products.

47

化學家可做的事?

更有效的合成方法

奈米催化劑

晶片

(微流管)合成系統

離子液體

超級吸附劑

等等

合成:水熱法、電化學

特性:穩定、水中分散

碳點

MCF-10A (A and B) and MCF-7 (C and D) cells treated with C-dots prepared

Preparation of C‐dots

Hydrothermal Calcination

(e. g. glycine, EDTA, APTMS) Ground Coffee

1. Wide varieties of resources 2. One-pot preparation

3. Fast (2 hr)

4. Green (no solvent & strong acid) 5. narrower size distribution

Large molecules (e. g. BSA)

Natural resource

300 °C, 2 hr

Heated in stainless steel

Temperature effect on the preparation of C-dots

Optical property of ground coffee C‐dots

Excitation wavelength dependence PL

is due to different sizes and surface

properties (the presence of various types of chromophores with different degrees of double bond conjugation and

C-dots induced (A) cytotoxicity, (B) oxidative stress, and (C) LDH release of MCF-10A, MCF-7 and MDA-MB-231 cells. 1× = 0.36 mg/mL. The percentages of cell viability, fold of ROS generation, and fold of LDH release are shown as a relative value to control (MCF-10A cells). The values represent (mean ± SD, n = 3, **p < 0.001, *p < 0.01).

J. Mater. Chem. B 2013, 1, 1774-1781.

Reactive oxygen species (ROS) generated; an oxidative stress mechanism

C-dots caused the inhibition of the cancer cells through apoptosis

Biosafety to normal cells, but inhibition of cancer cells

membrane binding without damage

Surface molecules such as

catechins must play some roles

Bright  field UV light  (360–380 nm)  Blue light  (460–480 nm) _{(510–530 nm)}Green light    

Carbon dots prepared from ginger exhibit efficient 

inhibition of human hepatocellular carcinoma cells 

Curcumin could trigger the pro-apoptotic

Tumor was formed by inoculating with 1 × 107 HepG2 cells C-dots (440 g) 3.7  0.2 mg 104  14 mg after 14-day

Increased p53 confirmed that the increased cellular level of ROS was responsible for killing HepG2 cells through apoptosis

λ_ex : 365 nm λ_em : 445 nm (+)-catechin Hydrothermal reduction 300℃/ 2h GO C-dots@RGO

Photoluminescent C-dots@RGO Probe for the Detection of Acetylcholine

TEM SEM

bright field 360–380 410–430 510–530

Excitation wavelength dependence of its PL properties _{Anal. Chem. 2013, 85, 3263−3270}

 H₂O₂(100 nM) in Tris-HCl buffer (25 mM, pH 9.0)

 I_PL0 and I_PL are the PL intensities of the solutions before and after the PL quenching reaction, respectively.

Betaine +

+ acetate

 Ach: neurotransmitter

 No electroactive, chromophore, or fluorophore group in ACh.

Selectivity

Detection of ACh Using C-dots@RGO

Linear range : 0.05–10 nM LOD : 30 pM

Detection of ACh in real samples

Blood

Plasma

2.6 ± 0.8 nM 6.8 ± 0.4 nM

SiC‐dots thin film temperature probe

Temperature-sensitive photoluminescence of organosilane-functionalized carbon dot films. The SiC-dot films were stable for at least 10 cycles of water washing, mainly

because of strong Si–O–Si interactions between the SiC-dots and the glass substrates.

57

59

卡西酮

海洛

因

古柯鹼

碳量子點於毒品檢測之應用

亦稱為β- 酮基安非他命:

新興精神作用

物質常以浴鹽（bath salts）

的名稱進行販賣。

Detection of 4-chloroethcathinone using C-dots. (A) Sensitivity for 4-chloroethcathinone at pH 11.0, and (B, C) selectivity of

4-溶液相檢測

61

試紙檢測

85 

170  

Nimetazepam

Conc. 

(μM)

32

64

Flunitrazepam

1 or 2 tablet in 200 mL

一粒眠

FM2

Conclusions:

1. 化學是很生活化的科學。

2. 化學不難且實用。

3. 強調低耗能和低毒性的綠色化學

是一門值得推廣的科學。

4.

奈米感測器可檢測多種分析物；

如碳點用於檢測毒品。