Multivalent Molecular Shuttles - Effect of Increasing the Number of Centers in Switchable Catalysts

被引:13
作者
Alvarez, Celedonio M. [1 ]
Barbero, Hector [1 ]
Miguel, Daniel [1 ]
机构
[1] Univ Valladolid, GIR MIOMeT, IU CINQUIMA Quim Inorgan, Fac Ciencias, E-47005 Valladolid, Spain
关键词
Organocatalysis; Click chemistry; Rotaxanes; Molecular shuttles; BONDING ROTAXANE; THIN-FILMS; DENDRIMERS; HALOGEN; DESIGN; LIGAND; LIGHT; RECOGNITION; NANOSWITCH; EFFICACIES;
D O I
10.1002/ejoc.201500942
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A family of three molecular shuttles based upon ammonium/triazolinium salt motifs with one, two, and three catalytic centers were prepared along with their corresponding non-interlocked threads. The switching process for all rotaxanes was tested through an in situ procedure in solution. Furthermore, their organocatalysis of two Michale-type reactions by iminium activation was tested to check whether the increase of the number of catalytic centers in the same shuttle is a decisive factor to improve their efficiencies compared with those of single-active-site organocatalytic shuttles under the same conditions.
引用
收藏
页码:6631 / 6640
页数:10
相关论文
共 103 条
[1]  
ACHAR S, 1994, ANGEW CHEM INT EDIT, V33, P847, DOI 10.1002/anie.199408471
[2]  
[Anonymous], 2014, MATH PROBL ENG
[3]   Acid-base controllable molecular shuttles [J].
Ashton, PR ;
Ballardini, R ;
Balzani, V ;
Baxter, I ;
Credi, A ;
Fyfe, MCT ;
Gandolfi, MT ;
Gómez-López, M ;
Martínez-Díaz, MV ;
Piersanti, A ;
Spencer, N ;
Stoddart, JF ;
Venturi, M ;
White, AJP ;
Williams, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) :11932-11942
[4]   Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine [J].
Astruc, Didier ;
Boisselier, Elodie ;
Ornelas, Catia .
CHEMICAL REVIEWS, 2010, 110 (04) :1857-1959
[5]   Covalent assembly-disassembly of poly(ether imine) dendritic macromolecular monomers and megamers [J].
Bagul, Rahul S. ;
Jayaraman, Narayanaswamy .
POLYMER, 2014, 55 (20) :5102-5110
[6]   Multivalent dendritic catalysts in organometallic catalysis [J].
Bagul, Rahul S. ;
Jayaraman, Narayanaswamy .
INORGANICA CHIMICA ACTA, 2014, 409 :34-52
[7]   Efficacies of multivalent vs monovalent poly(ether imine) dendritic catalysts within a generation in multiple C-C bond forming reactions [J].
Bagul, Rahul S. ;
Jayaraman, Narayanaswamy .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 701 :27-35
[8]  
Ballardini R, 2000, EUR J ORG CHEM, V2000, P591
[9]   PHOTOACTIVE [2]ROTAXANES - STRUCTURE AND PHOTOPHYSICAL PROPERTIES OF ANTHRACENE-STOPPERED AND FERROCENE-STOPPERED [2]ROTAXANES [J].
BENNISTON, AC ;
HARRIMAN, A ;
LYNCH, VM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5275-5291
[10]   Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis [J].
Bergbreiter, David E. ;
Tian, Jianhua ;
Hongfa, Chayanant .
CHEMICAL REVIEWS, 2009, 109 (02) :530-582