Charge-transfer interaction of 4,13-diamino[2.2]paracyclophane with π-acceptors

A General and a Simple Synthesis of {4-[(Z)-4-(Arylimino)-3,4-Dihydroquinazolin-2(1H)-Ylidene]Cyclohexa-2,5-Dien-1-Ylidene} Malononitrile from the Reaction of 2-Amino-N′-Arylbenzimidamides with 7,7,8,8-Tetracyanoquinodimethane

“…The reaction mixture was stirred at room temperature for 4-7 h. After completion of the reaction (the reaction was followed by TLC), the formed precipitate was collected by filtration, washed and recrystallised from DMF/EtOH to afford products 5a-g in 45-60 % yield. 10), 218 (12), 192 (10), 166 (12), 153 (8), 114 (6), 102 (12), 93 (8), 77 (10), 57 (6), 44 (18); Scheme 2 Reaction of 2-amino-Np-arylbenzimidamides (3a-g) with TCNQ ( 4).…”

“…10 This strategy is considered as an extension of our long-term interest in chemical reactions induced by charge-transfer complexation to obtain new heterocyclic systems. 11,12 TCNQ is a very known electron-acceptor molecule, which has been successfully used for preparation of electrically conducting salts and CTcomplexes. The interest of TCNQ has been focused on its potential application on molecules rectifiers, non linear optical materials, organic ferromagents, and organic chromophores with electron accepting properties.…”

Enantiospecific synthesis of [2.2]paracyclophane-4-thiol and derivatives

“…The close proximity of the arene moieties results in strong electronic and structural interactions between the two rings and between substituents appended to each layer [ 1 – 2 ]. The resulting unique properties have led to derivatives of [2.2]paracyclophane being employed in a wide range of disciplines including polymer, material and electronic chemistry [ 3 – 9 ]. Whilst enantiomerically pure derivatives have been utilised in chiral catalysis [ 10 – 11 ] and as probes for biological recognition processes [ 12 – 14 ], the full potential of these systems has not been realised due to the difficulties encountered when trying to access enantiomerically pure [2.2]paracyclophane derivatives [ 15 ].…”