The Chemistry of Tetracyanoethylene

Acenequinocumulenes: Lateral and Vertical π‐Extended Analogues of Tetracyanoquinodimethane (TCNQ)

“…[10][11][12][13] Organic semiconductors are often classified into two categories, p-type (donor,h ole conducting)a nd n-type (acceptor, electron conducting). [16][17][18][19] One of the mostc ommonn on-fullerene compound classes used as n-type semiconductorsa re cyano-based acceptors such as tetracyanoethylene (TCNE,F igure 1) [20][21][22][23] and the more stable, p-extended analogue tetracyanoquinodimethane (TCNQ). [16][17][18][19] One of the mostc ommonn on-fullerene compound classes used as n-type semiconductorsa re cyano-based acceptors such as tetracyanoethylene (TCNE,F igure 1) [20][21][22][23] and the more stable, p-extended analogue tetracyanoquinodimethane (TCNQ).…”

“…In the case of p-type organic semiconductors, many requisite properties have been fulfilled, [1,2,6,14,15] whereas the realizationo fn -type organic materials remainst roubled by issues such as complex synthesis,i nstability in air,poor solubility,l arge electron-injectionb arriers, and low charge carrierm obilities. [16][17][18][19] One of the mostc ommonn on-fullerene compound classes used as n-type semiconductorsa re cyano-based acceptors such as tetracyanoethylene (TCNE,F igure 1) [20][21][22][23] and the more stable, p-extended analogue tetracyanoquinodimethane (TCNQ). [24] First reported in 1960 by Acker et al, [25,26] pristine TCNQ has become one of the most extensively studied acceptor materials.…”

Pyridine-Functionalized MCM-41 as an Efficient and Recoverable Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems

“…TCNE has received an extensive amount of study and the chemistry of this compound has been reviewed several times. [8][9][10] The mesoporous molecular sieves such as MCM-41 which discovered by Mobil researchers in 1992, have large and uniform pore sizes, ultrahigh surface areas, large pore volume and rich silanol groups in the inner walls. The developments of mesoporous silicas such as MCM-41 have generated interest due to their potential applications such as catalysts, catalyst supports, separation media, and host materials for inclusion compounds.…”

Meldrum's Acid Catalyzed Reaction of Tetracyanoethylene and Aldehydes in Water: A Novel Approach to Arylidenemalononitrile

“…TCNE has received an extensive amount of study and the chemistry of this compound has been reviewed several times. [18][19][20] As a part of our current studies on the multi component reactions (MCRs), [21][22][23][24][25] and our interest in chemistry of TCNE, [26][27][28][29] we have investigated the possibility of trapping the heterodiene generated from the reaction of Meldrum's acid (1) and aldehydes 2 with TCNE 3. In the event we did not observe the expected MCR product 4; instead the reaction afforded the corresponding arylidenemalononitrile 5 with Meldrum's acid playing as a catalyst role in the reaction between the TCNE and various aldehydes.…”