Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes

Investigation of crystal structure, vibrational characteristics and molecular conductivity of 2,3-dichloro-5,6-dicyno-p-benzoquinone

“…These efforts were concentrated mainly on cation radical salts of tetrathiafulvalene derivatives, obtained by electrocrystallization with various anions acting as hydrogen bond or halogen bond acceptors. Halogen bonding interactions were also explored in charge-transfer salts [2][3][4]. According to Lieffrig et al [5] 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) acts as a powerful oxidant toward iodinated TTFs and the formation of novel charge-transfer salts with original halogen bonding patterns.…”

Synthesis and structure of bis(ethylenedioxy)‐1,4,5,8‐tetraselenanaphthalene

“…In the course of our study on π‐donors fused by a 1,4‐dioxene ring,[9] we investigated the synthesis of bis(ethylenedioxy)‐1,4,5,8‐tetraselenanaphthalene (BEDO‐TSeN) containing two fused 1,4‐dioxene rings. Since the ethylenedioxy unit in a π‐donor system is known to play a role by increasing either the donor property (inductive and mesomeric effects) or the stacking ability (CH···O hydrogen bond), TTFs and oligothiophenes having ethylenedioxy substituents have been employed for designing highly conducting materials [10].…”

Halogen Bonding Interactions in DDQ Charge Transfer Salts with Iodinated TTFs

“…Most examples rely on TTF derivatives functionalized with hydrogen bond donor groups (−CH 2 OH, −CONHR), and chemically oxidized with TCNQ [2] or TCNQF 4 [3,4]. Halogen bonding interactions were also explored in charge-transfer salts, particularly by Iyoda [5] and Bryce [6], as in (EDT-TTFCl 2 ) 2 (TCNQF 4 ) [7]. Note that, due to their strong electronegativity, the functionalization of the TTF core with electron-withdrawing halogen atoms rises the oxidation potential of the TTF molecules, making often impossible their oxidation with TCNQ itself whose reduction potential amounts to 0.17 V (vs. SCE).…”