A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes.

A series of donor-acceptor molecules, featuring intense low-energy intramolecular charge-transfer bands, was prepared by regioselective [2 + 2] cycloaddition between 7,7,8,8-tetracyanoquinodimethane (TCNQ) and N,N-dialkylanilino-substituted (DAA-substituted) alkynes, followed by ring opening of the initially formed cyclobutenes.

[1]  F. Diederich,et al.  Charge-transfer chromophores by cycloaddition-retro-electrocyclization: multivalent systems and cascade reactions. , 2007, Angewandte Chemie.

[2]  F. Diederich,et al.  Donor-substituted 1,1,4,4-tetracyanobutadienes (TCBDS): new chromophores with efficient intramolecular charge-transfer interactions by atom-economic synthesis. , 2006, Chemistry.

[3]  Joel S. Miller,et al.  M[TCNQ]y-Based Magnets (M = Mn, Fe, Co, Ni; TCNQ = 7,7,8,8-tetracyano-p-quinodimethane) , 2005 .

[4]  Ivan Biaggio,et al.  A new class of organic donor-acceptor molecules with large third-order optical nonlinearities. , 2005, Chemical communications.

[5]  Matthew Thorum,et al.  Vanadium 7,7,8,8-tetracyano-p-quinodimethane (V[TCNQ]2)-based magnets. , 2004, Inorganic chemistry.

[6]  J. Segura,et al.  Design and synthesis of TCNQ and DCNQI type electron acceptor molecules as precursors for 'organic metals' , 1997 .

[7]  W. Kaim,et al.  The coordination chemistry of TCNE, TCNQ and related polynitrileπ acceptors , 1994 .

[8]  J. Brédas,et al.  Donor-acceptor diphenylacetylenes : geometric structure, electronic structure, and second-order nonlinear optical properties , 1993 .

[9]  T. Itoh,et al.  p-Phenylenetetramethylene diradical and zwitterion intermediates in the spontaneous copolymerizations of electrophilic p-quinodimethanes with electron-rich olefins , 1990 .

[10]  M. Hanack,et al.  Syntheses and electrochemical properties of tetracyano-p-quinodimethane derivatives containing fused aromatic rings , 1989 .

[11]  M. Hanack,et al.  Synthesis and electrochemical properties of 15,15,16,16-tetracyano-6, 13-pentacenequinodimethane (TCPQ) , 1988 .

[12]  R. Huisgen Tetracyanoethylene and enol ethers. A model for 2 + 2 cycloadditions via zwitterionic intermediates , 1977 .

[13]  B. P. Bespalov,et al.  7,7,8,8-Tetracyanoquinodimethane in Addition, Substitution, and Complex Formation Reactions , 1975 .

[14]  John P. Ferraris,et al.  Electron transfer in a new highly conducting donor-acceptor complex , 1973 .

[15]  J. K. Williams Substituted Quinodimethanes. V.1 p-Tricyanovinylphenyldicyanomethide and Related Anions , 1962 .

[16]  W. R. Hertler,et al.  Substituted Quinodimethans. I. Preparation and Chemistry of 7,7,8,8-Tetracyanoquinodimethan , 1962 .

[17]  W. Mahler,et al.  Substituted Quinodimethans. II. Anion-radical Derivatives and Complexes of 7,7,8,8-Tetracyanoquinodimethan , 1962 .

[18]  W. R. Hertler,et al.  Substituted Quinodimethans. III. Displacement Reactions of 7,7,8,8-Tetracyanoquinodimethan , 1962 .

[19]  W. Mahler,et al.  7,7,8,8-TETRACYANOQUINODIMETHANE AND ITS ELECTRICALLY CONDUCTING ANION-RADICAL DERIVATIVES , 1960 .