Synthesis and properties of isoxazolo[60]fullerene -: Donor dyads

被引:65
作者
Langa, F [1 ]
de la Cruz, P
Espíldora, E
González-Cortés, A
de la Hoz, A
López-Arza, V
机构
[1] Univ Castilla La Mancha, Fac Ciencias Quim, Toledo 45071, Spain
[2] Univ Castilla La Mancha, Fac Ciencias Medio Ambiente, Toledo 45071, Spain
[3] Univ Castilla La Mancha, Escuela Ingn Tecn Ind, Toledo 45071, Spain
[4] Univ Complutense, Fac Quim, E-28040 Madrid, Spain
关键词
D O I
10.1021/jo0010532
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of isoxazolo[60]fullerenes has been prepared in one pot from aldoximes under microwave irradiation. Several donors and accepters were used as Substituents. The absorption and emission spectra of these compounds in polar solvents suggest a weak charge-transfer interaction between the oxygen atom of the isoxazoline moiety and the C-60 cage, as well as a stronger interaction between the donor and the fullerene cage when the attached groups are p-N,N-dimethylaniline or ferrocene. The electrochemical properties of the compounds were investigated and they Show the same or better acceptor character than C-60 in all cases. Theoretical calculations support the results obtained; Solvent effects in the H-1 NMR spectra have been determined and provide useful information concerning the polarization of dyads.
引用
收藏
页码:8675 / 8684
页数:10
相关论文
共 42 条
[1]  
Almena I, 1999, TARG HETEROCYCL SYST, V2, P281
[2]   H-1-NMR AND C-13-NMR SPECTRA OF PHENYL-SUBSTITUTED AZOLE DERIVATIVES .2. CONFORMATIONAL STUDY [J].
BEGTRUP, M .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (01) :61-77
[3]   Large quadratic hyperpolarizabilities with donor-acceptor polyenes exhibiting optimum bond length alternation: Correlation between structure and hyperpolarizability [J].
BlanchardDesce, M ;
Alain, V ;
Bedworth, PV ;
Marder, SR ;
Fort, A ;
Runser, C ;
Barzoukas, M ;
Lebus, S ;
Wortmann, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (07) :1091-1104
[4]   ELECTROCHEMISTRY OF MONO-ADDUCTS THROUGH HEXAKIS-ADDUCTS OF C-60 [J].
BOUDON, C ;
GISSELBRECHT, JP ;
GROSS, M ;
ISAACS, L ;
ANDERSON, HL ;
FAUST, R ;
DIEDERICH, F .
HELVETICA CHIMICA ACTA, 1995, 78 (05) :1334-1344
[5]  
BRADY G, 1960, J AM CHEM SOC, V82, P1927
[6]   O-CARBAMOYLOXIMES [J].
DALTON, DR ;
FOLEY, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (24) :4200-4203
[7]  
DaRos T, 1997, CHEM COMMUN, P59
[8]   Electroactive 3-(N-phenylpyrazolyl)isoxazoline[4′,5′:1,2][60]fullerene dyads [J].
de la Cruz, P ;
Espíldora, E ;
García, JJ ;
de la Hoz, A ;
Langa, F ;
Martín, N ;
Sánchez, L .
TETRAHEDRON LETTERS, 1999, 40 (26) :4889-4892
[9]   Templated regioselective and stereoselective synthesis in fullerene chemistry [J].
Diederich, F ;
Kessinger, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (06) :537-545
[10]   Cycloaddition of C-60 fullerene to stable 2-RSO2-benzonitrile oxides [J].
Drozd, VN ;
Knyazev, VN ;
Stoyanovich, FM ;
Dolgushin, FM ;
Yanovsky, AI .
RUSSIAN CHEMICAL BULLETIN, 1997, 46 (01) :113-121