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2015 Vol. 23, No. 12
Published: 2015-12-20
1085
Synthesis and Antitumor Activities of Novel Aryl-substituted Gambogic Acid Derivatives
ZHANG Zhi-jia, LI Jin-hai, CHEN Mei-jun, HUANG Yan, ZHAO Lu-ning
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1085
Aryloxy(heterocyclic)-alcohol(
2a~2k
) were prepared by Williamson ether reaction of substituted phenols(or hydroxypyridines) with bromo-alcohol, using K
2
CO
3
as alkali. Gambogic acid derivatives(
3a~3k
) were synthesized by Mitsunobu reaction of
2a~2m
with gambogic acid, respectively. Arycarbonylamibo alcohols(
5a~5h
) were prepared by coupling reaction of aromatic acid with 3-amino-1-propanol, using DDC/HOSu as coupling agent. Gambogic acid derivatives(
6a~6h
) were synthesized by Mitsunobu reaction of
5a~5h
with gambogic acid, respectively.
2, 3, 5
and
6
were new compounds and the structures were characterized by
1
H NMR, ESI-MS and HR-MS. The
in vitro
antitumor activities of
3
and
6
against human lung cancer cells(A549), human liver cancer cells(HepG-2) and human breast cancer cells(SK-BR-3) were investigated by MTT method. The results showed that some of the compounds exhibited better antitumor activities than gambogic acid.
2015 Vol. 23 (12): 1085-1094 [
Abstract
] (
509
)
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(1 KB)
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(969 KB) (
388
)
1095
Synthesis and Cytotoxic Activities of 2,5-Diketopiperazine Derivatives by One-pot Method
LI Jin-sheng, LIAO Sheng-rong, TANG Yong, LIU Yong-hong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1095
Ten 2,5-diketopiperazine derivatives(
4a~4j, 4c,
4f
and
4i
were novel compounds) in yield of 54.2~75.7% were synthesized by Aldol reaction of
N,N
-diacetyl-2,5-diketopiperazine, arylaldehyde and RX by onepot method, using DMF as the solvent and Cs
2
CO
3
as the alkali. The structures were confirmed by
1
H NMR,
13
C NMR and ESI-MS. Preliminary biological activities tests indicated that (Z)-1-acetyl-4-allyl-3-(naphthalen-1-ylmethylene)piperazine-2,5-dione(4
c
) exhibited better cytotoxic activities against U937, Hela and Du145 cell lines.
2015 Vol. 23 (12): 1095-1099 [
Abstract
] (
684
)
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(1 KB)
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(1145 KB) (
463
)
1100
Synthesis and Antifungal Activities of Novel Thiochromanone Derivatives Containing 1,3,4-Thiadiazole
LIANG Guo-chao, ZHOU Guan, ZHONG Yi-fan, HAN Xiao-yan, SONG Ya-li
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1100
4-Thiochromane-2-carboxylic acid derivatives(
2a~2d
) were prepared by Michael addition reaction of substituted thiophenol with maleic anhydride. 2-(5-amino-1,3,4-thiadiazol-2-yl)thiochroman-4-one derivatives(
3a~3d
) were prepared by acylation reaction of 2
a~22d
with thiosemicarbazide, respectively. Fourteen novel thiochromanone derivatives(
5a~5n
) containing 1,3,4-thiadiazole were synthesized by reaction of
3a~3d
with acyl chloride. The structures were characterized by
1
H NMR,
13
C NMR and HR-ESI-MS. The antifungal activities of
5a~5n
were investigated by micro dilution method. The results showed that some derivatives exhibited better antifungal activities on
Epidermophyton floccosum
and
Mucor racemosus
than Fluconazole.
2015 Vol. 23 (12): 1100-1105 [
Abstract
] (
333
)
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(1 KB)
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(780 KB) (
330
)
1106
Synthesis and Anti-tumor Activities of Novel Steroidal
N,N
-dimethylthiosemicarbazone Compounds
HUANG Yan-min, ZHENG Jia-hua, ZHAO Dan-dan, QI Bin-bin, YANG Chunhui, SHENG Hai-bing, GAN Chun-fang, CUI Jian-guo
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1106
Four novel
N,N
-dimethylthiosemicarbazone compounds(
1~4
) were synthesized by condensation reaction of dehydroepiandrosterone, pregnenolone, estrone, 3,5-dihydroxy-6-formyl-B-norcholestane with
N,N
-dimethylthiosemicarbazide, respectively, using EtOH(or MeOH) as solvent and HAc as catalyst. The structures were characterized by
1
H NMR,
13
C NMR, IR and HR-EI-MS. The anti-tumor activities of
1~4
against human hepatoma cells(HepG), nasopharyngeal carcinoma cells(CNE-2) and normal kidney epithelial cells(HEK293T) were investigated by MTT method. The results showed that
1~3
had better antiproliferative activities against HepG and CNE-2.
2015 Vol. 23 (12): 1106-1110 [
Abstract
] (
483
)
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(1 KB)
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(698 KB) (
504
)
1111
A Novel Method for Preparing Poly(L-lactic acid-co-glycolic acid) and Poly(D-lactic acid) Stereocomplexes
DONG Jun, BAI Wei, HUANG Dong-ling, XIONG Cheng-dong
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1111
Stereocomplexes(sc-PLA) was prepared by improved solvent method, using high molecular weight poly(L-lactic acid-co-glycolic acid)(PLLGA) and poly(D-lactic acid)(PDLA)[
m
(PLLGA) :
m
(PDLA)=3:1,
c
50 mL·g
-1
]as materials, chloroform as solvent and equal volume methanol as precipitator, at 50 ℃ for 4 h. The structure and performances were characterized by XRD, DSC and TGA. The crystallinity and initial decomposition temperature of sc-PLA were 96.2% and 342 ℃, respectively.
2015 Vol. 23 (12): 1111-1115 [
Abstract
] (
418
)
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(1 KB)
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(1247 KB) (
328
)
1116
Synthesis of Novel Asymmetric Crown-annelated Tetrathiafulvalene Derivatives and Their Responsive Properties on Alkali Metal Ions
ZHANG Rui, GU Xiao-long, JI Yong, XU Ming
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1116
Four new asymmetric crown-annelated tetrathiafulvalene derivatives(3a~3c and 4) were synthesized by coupling reaction of 4,5-bis(cyanoethylthio)-(ethylenedithio)tetrathiafulvalene(
1a
), 4,5-bis(cyanoethylthio)-methylethylene-dithiatetrathiafulvalene(
1b
), 4,5-bis(cyanoethylthio)-propylenedithiatetrathiafulvalene(
1c
), 4,5-bis(cyanoethylthio)-bnezodithiatetrathiafulvalene(
2
) with penta-(ethyl-eneglycol)di-p-toluenesulfonate in solution of CsOH and MeOH/DMF, respectively. The structures were characterized by
1
H NMR,
13
C NMR, ESI-MS and elemental analysis. Electrochemical responsive properties of
3a~3c
and
4
on alkali metal cations(Na
+
, Li
+
, K
+
, Rb
+
) were investigated by cyclic voltammogram method. The results showed that 2,3-dithia-(3′,6′,9′,12′-tetraoxatetradecyl)-6,7-propylenedithiatetrathiafulvalene(
3c
) and 2,3-dithia-(3′,6′,9′,12′-tetraoxatetradecyl)-6,7-benzodithiatetrathiafulvalene(
4
) are responsive for Na
+
with 30 mV and 45 mV of △E
1/2
1
, respectively.
2015 Vol. 23 (12): 1116-1119 [
Abstract
] (
418
)
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(1 KB)
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(923 KB) (
421
)
1120
Synthesis and Fluorescent Properties of 7-{[2-(8-Hydroxyquinolin-7-yl)-1
H
-benzo[
d
]imidazole-1-yl]-methyl}quinolin-8-ol and Its Metal Complexes
LIU Hong, LI Chuang-hai, LIAO Ya-si
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1120
A novel ligand, 7-{[2-(8-Hydroxyquinolin-7-yl)-1
H
-benzo[
d
]imidazole-1-yl]methyl}quinolin-8-ol(H
2
L), was synthesized by condensation reaction of 8-hydroxyquinoline-7-carbaldehyde with
o-
phenylenediamine. Two novel metal complexes, ZnL·H
2
O(
1
)and Al
2
L
3
·3H
2
O(
2
), were synthesized by coordination reaction of H2L with Ac
2
Zn·2H
2
O and AlCl
3
·6H
2
O, respectively. The structures and properties were characterized by UV-Vis,
1
H NMR, IR, elemental analysis and FL.
λ
em
of
1
and
2
were 514 nm(
λ
ex
=400 nm) and 525 nm(
λ
ex
=401 nm), respectively.
2015 Vol. 23 (12): 1120-1123 [
Abstract
] (
375
)
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(1 KB)
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(1233 KB) (
429
)
1124
Synthesis and Anticancer Activities of Novel Oxovanadium(IV) Complexes[VO(dtbsal-met)(phen) and VO(naph-met)(phen)]
CAO Ya-ping, YI Cen-lan, LIU Hong-mei,LI Hai-xia, ZUO Jian-li, YUAN Ze-li
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1124
Two novel oxovanadium(IV) complexes, VO(dtbsal-met)(phen)(
1
) and VO(naph-met)(phen)(
2
), were synthesized by aldimine condensation reaction reaction, using L-methionine(meth), 1,10-phenanthroline(phen), 3,5-di-
tert
-butyl salicylaldehyde(dtbsali)[or 2-hydroxy-1-naphthaldehyde(hnaph)] as materials. The structures were characterized by IR, HR-ESI-MS, molar conductance and single-crystal X-ray.
1
(CCDC:1 429 158) and
2
(CCDC:1 429 159)belongs to monoclinic crystal system and triclinic system, respectively. The
in vitro
anticancer activities of
1
and
2
against A549 and HeGp2 were tested by MTT method. The results showed that
1
and
2
exhibited certain antitumor activities.
2015 Vol. 23 (12): 1124-1129 [
Abstract
] (
454
)
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(1 KB)
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(1101 KB) (
446
)
1130
Synthesis of Two Novel Diacetylene Derivatives
CHEN Bei-hua, ZHANG Zhen, ZHANG Deng-qing,LI Xian-ying, XIANG Yun-jie, JIN Wu-song
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1130
A novel diacetylene derivative(
1
) was synthesized by improved Glasercoupling reaction(CuI as catalyst and Et
3
N as solvent) of 3-ethynyl-5-(3-methyl-3-hydroxyl)-butynyl-1-(3-dodecyloxy)-2-{[(dodecyloxy)methyl]propoxy}benzene(
6
), which was obtained by selective Sonogashira reaction, Sonogashiracoupling reaction and deprotection from 3,5-dibromo-1-{3-(dodecyloxy)-2-[(dodecyloxyyl)methyl]propoxy}benzene and 2-methyl-3-butyn-2-ol. A novel diacetylene derivative(
2
) was synthesized by Sonogashira reaction, THP deprotection reaction and improved Glasercoupling reaction from
6
and 2,2′-[(2,5-diiodo-1,4-phenylene)bis(oxy)]bis(tetrahydro-2
H
-pyran). Structures of intermediate,
1
and
2
were characterized by
1
H NMR,
13
C NMR and MALDI-TOF-MS.
2015 Vol. 23 (12): 1130-1134 [
Abstract
] (
406
)
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(1 KB)
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(815 KB) (
414
)
1135
Synthesis of Novel Xanthene-dione Derivatives Containing 2-Quinolone Moiety
WANG Xuan, ZHANG Zhen-ming, WANG Run-nan, ZHANG Dan-dan, LI Shu-an
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1135
Five novel xanthene-dione derivatives containing 2-quinolone moiety were synthesized in yields of 78%~90% by reaction of substituted 2-chloroquinoline-3-carbaldehyde with 5,5-dimethyl-1,3-cyclohexanedione, using acetic acid as catalyst and DMF as solvent at 80 ℃~100 ℃ for 2.5 h~4.0 h.The structures were characterized by
1
H NMR, IR, HR-ESI-MS and elemental analysis. X-ray single crystal diffractometer of 3,3,6,6-tetramethyl-9-{3-[7-methylquinolyl-2(1
H
)-one]}-2,4,5,7,9,10-hexahydro-xantene-1,8(2
H
,5
H
)-dione(
3b
) tests indicated that
3b
(CCDC: 971 833) belongs to monoclinic crystal system, space group
C
12/
C
1 with
a
=1.411 90(16)nm,
b
=2.231 4(2)nm,
c
=1.618 28(18)nm,
β
=106.904°,
V
=4.878 1(9) nm
3
,
Dc
=1.175 g·cm
-3
,
Z
=1,
R
1
=0.044 4,
wR
2
=0.074 6.
2015 Vol. 23 (12): 1135-1139 [
Abstract
] (
438
)
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(1 KB)
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(1053 KB) (
461
)
1140
Synthesis of Novel
α
-Aminophosohonate Derivatives Containing 6-(4-Aminophenyl)-4,5-dihydro-3(2
H
)pyridazinone
JU Zhi-yu, NIU Liang-feng, LI Fu-yuan, LI Gong-chun, WU Chang-zheng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1140
Five novel
α
-aminophosohonate derivatives containing 6-(4-aminophenyl)-4,5-dihydro-3(2
H
)pyridazinone were synthesized by Mannichtype reaction of aromatic aldehyde, diethyl phosphite and 6-(4-aminophenyl)-4,5-dihydro-3(2
H
)-pyridazinone, which was prepared by Friedel-Crafts acylation, amide hydrolysis and condensation, using acetylaniline and succinic anhydride as starting materials. The structures were characterized by
1
H NMR,
13
C NMR,
31
P NMR, IR and ES-MS
2015 Vol. 23 (12): 1140-1142 [
Abstract
] (
378
)
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(1 KB)
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(707 KB) (
348
)
1143
Synthesis and Surface Photoelectric Property of a Novel One-dimensional Cobalt Complex with (4,4)-Connect (4
4
·6
2
) Topology Structure
LI Jia-ming, SHI Zhong-feng
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1143
A novel 1D chain cobalt complex, [Co(4,4′-bipy)
3
(OH)
2
]
n
(
1
), was synthesized by solvent evaporation method, using Co(NO
3
)
2
·6H
2
O, 1
H
-benzotriazole-1-acetic acid and 4,4′-bipyrine(4,4′-bipy) as materials. The structure was characterized by FT-IR, elemental analysis, X-ray single crystal diffraction.
1
belongs to monoclinic and space group
C2/c
with
a
=18.057(4) ,
b
=11.487(2) ,
c
=24.590(5) ,
β
=93.60(3)°,
V
=5 090.4(18)
3
,
Z
=4,
Dc
=0.733 g·cm
-3
,
μ
=0.358 mm
-1
,
F
(000)=1 144,
R
1
=0.093 0,
ωR
2
=0.192 2.
1
was in distorted octahedral configuration with a central ion[Co(Ⅱ)]-coordinated with four N and two O. 2D(4,4)-connect (4
4
·6
2
) topological supramolecular network was constructied by intermolecular hydrogen bonding(O-H┈N) and
π…π
stack interactions formed by non-bridged 4,4′-bipys. The SPS results indicated that
1
exhibited photovoltaic conversion propertity with positive surface photovoltage responses in 300 nm~600 nm.
2015 Vol. 23 (12): 1143-1146 [
Abstract
] (
367
)
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(1 KB)
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(1171 KB) (
362
)
1147
Synthesis of a Novel Phenanthroline Derivative
LI Rong, WANG Qiang, ZHANG Deng-qing, LI Xian-ying, XIANG Yun-jie, JIN Wu-song
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1147
2,2′-【2,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-1,4-phenylene】bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane(
6
) was prepared by a two-step reaction from 2-[2-(2-methoxyethoxy)ethyl]-1,4-methylbenzene sulfonate. A novel phenanthroline derivative, 3,3′-【2,5-bis{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-1,4-phenylene】bis(1,10-phenanthrdin), was synthesized by Suzuki coupling reaction of 3-bromo-1,10-phenanthrdine with
6
. The stucture was characterized by
1
H NMR and MALDI-TOF-MS.
2015 Vol. 23 (12): 1147-1149 [
Abstract
] (
545
)
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(1 KB)
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(667 KB) (
513
)
1150
Synthesis of 3-Substituted 3-phenyl-1-indanone Compounds
WANG Ze-yu, DING Gang, YIN Zhong-qiong, YUE Gui-zhou
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1150
Four 3-substituted-3-phenyl-1-indanone compounds(
3a~3d, 3b~3d
were novel compounds) were synthesized by nucleophilic substitution reaction of 3-phenyl-1-indanone(
1
) with iodides(RI), using LDA as base and THF as solvent. The structures were characterized by
1
H NMR,
13
C NMR and EI-GC-MS. The yield of
3a~3d
were 70%~80% under the optimum reaction conditions(
1
1.0 eq., LDA/RI=2.1/1.5, at 0 ℃~rt for 5 h).
2015 Vol. 23 (12): 1150-1152 [
Abstract
] (
519
)
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(1 KB)
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(835 KB) (
606
)
1153
Research of Synthetic Process of Sodium 3-Chloro-2-hydroxy Propanesulfate
GE Li-juan, LIU Bai-ling, ZHANG Yong,LI Chen-ying, LUO Rong, CHEN Hua-lin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1153
A important intermediate of sulfonate amphoteric surfactant, sodium 3-chloro-2-hydroxy propanesulfate(
2
), was synthesized by acidcatalyted ringopening reaction, using epichlorohydrin(
1)
and NaHSO
3
as material, Na
2
SO
3
as initiator, EDTA
2
Na as complexing synergist. The structure was confirmed by
1
H NMR, IR and ESI-MS. The yield of
2
was 81.55% under the optimum reaction conditions[
1
0.55 mol,
n
(NaHSO
3
):
n
(Na
2
SO
3
):
n
(EDTA
2
Na):
n
(H
2
O)=1.00 : 0.04 : 0.01 : 9.50, dropping time of
1
was 15 min, rotating speed is varied from 100 rpm to 300 rpm, at 70 ℃ for 1.25 h].
2015 Vol. 23 (12): 1153-1157 [
Abstract
] (
505
)
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(1 KB)
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(957 KB) (
383
)
1158
Study on PEGfunctionlized
N
-heterocyclic Carbene-phosphine Palladium Catalyst for Suzuki CouplingReaction in Aqueous Phase
JIA Li
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1158
Studies of PEGfunctionlized
N-
heterocyclic carbenephosphine palladium catalyst[Cat(n=15)] for coupling 4-bromotoluene(
1
) with phenylboronic acid(
2
) in aqueousphase have been carried out. Effects of PEG kinds and amount, Cat dosage on Suzuki coupling were investigateed. The results showed that 50%PEG400 as co-solvent, the catalytic activities of Cat was similar with in 1,4-dioxane, and the conversion of
1
was nearly 100% at 110 ℃ for 3 h at loading of 0.1 mol%, and was 57% at 0.01 mol% at 110 ℃ for 21 h(TON 5 700). It was found that the Cat can be recycled and reused once at loading of 0.1 mol%.
2015 Vol. 23 (12): 1158-1161 [
Abstract
] (
322
)
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(1 KB)
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(878 KB) (
467
)
1162
Selective Synthesis of
β
-Benzildioxime
SHI Zhao-rui, LI Guo-hua, ZHANG Wen-bo
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1162
α
-Benzildioxime(
α
-
1
) and
β
-benzildioxime(
β
-
1
) were prepared by nucleophilic addition reaction of benzil(
2
) and hydroxylamine hydrochloride(
3
). The structures were confirmed by
1
H NMR and IR. Under optimum conditions[
2
10 mmol,
n
(
2
) :
n
(
3
)=1:5, methylbenzene as solvent, triethylamine as acid binding agent, dropping time of
3
was 4 h and pH=8, at 55 ℃ for 5.5 h], the yield of β-
1
was 90.4%.
2015 Vol. 23 (12): 1162-1165 [
Abstract
] (
333
)
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(1 KB)
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(1867 KB) (
333
)
1166
Preparation of Graphene
ZHANG Lan-qin, ZHAN Xiao-yuan, WANG Jie, ZHANG Zhi-hui, XU Guo-gang
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1166
Graphene(GN) was prepared by high temperature(1 050 ℃) oxidation reduction method, using spherical graphite as raw materials, HClO
4
as intercalator and KClO
3
as oxidant. The structure and properties were characterized by FT-IR, XRD, SEM, TEM, BET and RS. Effect of KClO
3
adding amount on the structure and performance of GN were investigated. When the dosage of KClO
3
is 0.08 g·mL
-1
, GN have best performance that the surface area is 558 m
2
·g
-1
, the average pore size is 3.012 nm and the resistivity is 0.02 Ω·cm.
2015 Vol. 23 (12): 1166-1170 [
Abstract
] (
730
)
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(1 KB)
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(2024 KB) (
1176
)
1171
Synthesis of 5-Substituted-2,3-dihydro-1
H
-[1,4]diazepine Compounds
CHEN Qi-fan, ZHANG Hui-dong, WU Xiao-yan, LIU Fei
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1171
Seven 5-substituted-2,3-dihydro-1
H
-[1,4]diazepine compounds(
3a~3g, 3a~3d
were novel compounds) were synthesized by Michael nucleophilic addition reaction of enaminone(
1
) with ethylene diamine(
2
) in ethanol. The structures were characterized by
1
H NMR, IR and elemental analysis. The yields of
3a~3g
were 70.0%~74.2% under the optimum reaction conditions[
1
30 mmol,
n
(
2
):
n
(
1
)=1.2, reflux 8 h~10 h, absolute alcohol as recrystallization solvent].
2015 Vol. 23 (12): 1171-1174 [
Abstract
] (
476
)
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(1 KB)
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(756 KB) (
324
)
1175
Synthesis and Anti-inflammatory Activities of Oxazolone Compounds
SUN Yin-xing, XU Guang-lin, HOU Bing-bo, AO Gui-zhen
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1175
Eight oxazolone compounds(
3a~3h
) were synthesized by Erlenmeyer cyclization of hippuric acid with substituted benzaldehyde. The structures were confirmed by
1
H NMR, FT-IR and HR-MS. The results of anti-inflammation by xyleneinduced mice ear edema suggested that
3f
[4-(3,5-dimethoxy-benzylidene)-2-phenyl-4
H
-5-oxazolone] exhibited better anti-inflammatory activity(50.3%) than aspirin(41.5%).
2015 Vol. 23 (12): 1175-1177 [
Abstract
] (
416
)
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(1 KB)
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(764 KB) (
353
)
1178
Hydrothermal Preparation and Properties Research Progressof Spinel Ferrite Hollow Nanomicrospheres
HE Fei, YAN Gong-qin
DOI: 10.15952/j.cnki.cjsc.1005-1511.2015.12.1178
The hydrothermal synthetic method, magnetic properties and electrochemical properties of spinel ferrite hollow nanomicrospheres, including 1D, 2D and multivariate spinel ferrite hollow anomicrospheres, are reviewed with 36 references. Future research orientation and application prospect are proposed.
2015 Vol. 23 (12): 1178-1183 [
Abstract
] (
564
)
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(1 KB)
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(4190 KB) (
692
)
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