Donor/acceptor fulleropyrrolidine triads

被引:87
作者
Herranz, MA
Illescas, B
Martín, N [1 ]
Luo, CP
Guldi, DM
机构
[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] Univ Notre Dame, Radiat Lab, Notre Dame, IN 46556 USA
关键词
D O I
10.1021/jo0005767
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New C-60-based triads, constituted by a fulleropyrrolidine moiety and two different electroactive units [donor I-donor 2 (10, 15a,b), or donor 1-acceptor (17, 21)], have been synthesized by 1,3-dipolar cycloaddition reaction of azomethyne ylides to C-60 and further acylation reaction on the pyrrolidine nitrogen. The electrochemical study reveals some electronic interaction between the redox-active chromophores. Triads bearing tetrathiafulvalene (TTF) and ferrocene (Fe) (10) or pi-extended TTFs and Fe (15a,b) show reduction potentials for the C-60 moiety which are cathodically shifted in comparison to the parent C-60 In contrast, triads endowed with Fe and anthraquinone (AQ) (17) or Fe and tetracyanoanthraquinodimethane (TCAQ) (21) present reduction potentials for the C-60 moiety similar to C-60 Fluorescence experiments and time-resolved transient absorption spectroscopy reveal intramolecular electron transfer (ET) processes from the stronger electron donor (i.e., TTF or extended TTF) to the fullerene singlet excited state, rather than from the poorer ferrocene donor in 10, 15a,b. No evidence for a subsequent ET from ferrocene to TTF.+ or pi-extended TTF.+ was observed.
引用
收藏
页码:5728 / 5738
页数:11
相关论文
共 51 条
[1]   2 DIFFERENT FULLERENES HAVE THE SAME CYCLIC VOLTAMMETRY [J].
ALLEMAND, PM ;
KOCH, A ;
WUDL, F ;
RUBIN, Y ;
DIEDERICH, F ;
ALVAREZ, MM ;
ANZ, SJ ;
WHETTEN, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1050-1051
[2]  
AUMULLER A, 1984, LIEBIGS ANN CHEM, P618
[3]   ELECTRICAL AND MAGNETIC-PROPERTIES AND X-RAY STRUCTURE OF A HIGHLY CONDUCTIVE 4-1 COMPLEX OF TETRACYANOQUINODIMETHANE AND A TETRATHIAFULVALENE DERIVATIVE [J].
BRYCE, MR ;
MOORE, AJ ;
HASAN, M ;
ASHWELL, GJ ;
FRASER, AT ;
CLEGG, W ;
HURSTHOUSE, MB ;
KARAULOV, AI .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (12) :1450-1452
[4]   Enhanced acceptor character in fullerene derivatives. Synthesis and electrochemical properties of fulleropyrrolidinium salts [J].
Da Ros, T ;
Prato, M ;
Carano, M ;
Ceroni, P ;
Paolucci, F ;
Roffia, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (45) :11645-11648
[5]   Electrochemistry of fullerenes and their derivatives [J].
Echegoyen, L ;
Echegoyen, LE .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (09) :593-601
[6]  
Effenberger F, 1998, SYNTHESIS-STUTTGART, P1372
[7]   ELECTROCHEMICAL EVIDENCE FOR THROUGH-SPACE ORBITAL INTERACTIONS IN SPIROMETHANOFULLERENES [J].
EIERMANN, M ;
HADDON, RC ;
KNIGHT, B ;
LI, QC ;
MAGGINI, M ;
MARTIN, N ;
OHNO, T ;
PRATO, M ;
SUZUKI, T ;
WUDL, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (15) :1591-1594
[8]   Thermal and microwave-assisted synthesis of Diels-Alder adducts of [60]fullerene with 2,3-pyrazinoquinodimethanes: Characterization and electrochemical properties [J].
FernandezPaniagua, UM ;
Illescas, B ;
Martin, N ;
Seoane, C ;
delaCruz, P ;
delaHoz, A ;
Langa, F .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3705-3710
[9]   PHOTOINDUCED ELECTRON-TRANSFER IN THE SOLID-STATE - RATE VS FREE-ENERGY DEPENDENCE IN FIXED-DISTANCE PORPHYRIN ACCEPTOR MOLECULES [J].
GAINES, GL ;
ONEIL, MP ;
SVEC, WA ;
NIEMCZYK, MP ;
WASIELEWSKI, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :719-721
[10]  
Garin J., 1993, SYNTHESIS-STUTTGART, P489