Methanofullerenes from macrocyclic malonates

被引:18
作者
Carano, M
Corvaja, C
Garlaschelli, L
Maggini, M
Marcaccio, M
Paolucci, F
Pasini, D
Righetti, PP
Sartori, E
Toffoletti, A
机构
[1] Univ Pavia, Dept Organ Chem, I-27100 Pavia, Italy
[2] Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy
[3] Univ Padua, Dept Phys Chem, I-35131 Padua, Italy
[4] Univ Padua, Dept Organ Chem, I-35131 Padua, Italy
关键词
EPR spectroscopy; fullerenes; membranes; sensors; supramolecular chemistry;
D O I
10.1002/ejoc.200390044
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
In this paper we describe the synthesis and intercomparison of several new methanofullerenes, each bearing a macrocyclic crown ether containing a malonate moiety directly attached to the C-60-fullerene core. Their complexing abilities with primary alkylammonium ions were investigated by NMR and mass spectrometry, and also by transport experiments through a liquid membrane. We also report on their electrochemical behaviour, together with EPR analysis of their supramolecular complexes with alkyl ammonium molecules labelled with a stable nitroxide radical. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码:374 / 384
页数:11
相关论文
共 75 条
[1]
Synthesis and liquid membrane transport properties of photolabile molecular clips based on dithiane-spiro-crown ethers [J].
Barnhurst, LA ;
Kutateladze, AG .
ORGANIC LETTERS, 2001, 3 (17) :2633-2635
[2]
BENCINI A, 1990, EPR EXCHANGE COUPLED, P53
[3]
SYNTHESES AND COMPLEXING PROPERTIES OF OXO-12-CROWN-3 AND OXO-18-CROWN-5 [J].
BERESFORD, GD ;
STODDART, JF .
TETRAHEDRON LETTERS, 1980, 21 (09) :867-870
[4]
Reductive electrolysis of [60]fullerene mono-methanoadducts in THF leads to the formation of bis-adducts in high yields [J].
Beulen, MWJ ;
Rivera, JEA ;
Herranz, MA ;
Martín-Domenech, A ;
Martín, N ;
Echegoyen, L .
CHEMICAL COMMUNICATIONS, 2001, (05) :407-408
[5]
Adduct removal from methanofullerenes via reductive electrochemistry [J].
Beulen, MWJ ;
Echegoyen, L ;
Rivera, JA ;
Herranz, MA ;
Martín-Domenech, A ;
Martín, N .
CHEMICAL COMMUNICATIONS, 2000, (11) :917-918
[6]
Blank A, 2000, J PHYS CHEM A, V104, P794, DOI 10.1021/jp9923791
[7]
A NOVEL RADICAL-TRIPLET PAIR MECHANISM FOR CHEMICALLY-INDUCED ELECTRON POLARIZATION (CIDEP) OF FREE-RADICALS IN SOLUTION [J].
BLATTLER, C ;
JENT, F ;
PAUL, H .
CHEMICAL PHYSICS LETTERS, 1990, 166 (04) :375-380
[8]
Effect of LiF/metal electrodes on the performance of plastic solar cells [J].
Brabec, CJ ;
Shaheen, SE ;
Winder, C ;
Sariciftci, NS ;
Denk, P .
APPLIED PHYSICS LETTERS, 2002, 80 (07) :1288-1290
[9]
NEW CLASS OF MACROCYCLIC ETHER-ESTER LIGANDS [J].
BRADSHAW, JS ;
HANSEN, LD ;
NIELSEN, SF ;
THOMPSON, MD ;
REEDER, RA ;
IZATT, RM ;
CHRISTENSEN, JJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (21) :874-875
[10]
THE SYNTHESIS OF SOME SUBSTITUTED MACROCYCLIC POLYETHER-DIESTER COMPOUNDS WITH THE MALONYL MOIETY [J].
BRADSHAW, JS ;
JOLLEY, ST ;
JONES, BA .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (06) :1317-1318