New synthesis and properties of 11,11,12,12-tetracyano-9,10-anthraquinodimethane: an electron acceptor displaying a single-wave, two-electron reduction and a coproportionation pathway to the radical anion

Abstract

Die Titelverbindung (VIIa) wird ausgehend vom Dicyanid (I) synthetisiert [die Zwischenstufe (V) ist labil und geht leicht ‐ in polaren Solventien oder ‐ z.T. ‐ beim Umkristallisieren in (VI) über; (VIIa) ist dann gleichermaßen aus (V) oder aus (VI) zugänglich].

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

“…Because the pendent substituents on the tail of 1a and 1c are distanced from the acene core by the [3]cumulene moiety,t he bending is less that of TCAQ (a = 144.68), [35] TCTQ (a = 135.98), [50] and TCPQ (a = 132.48) [50] as summarized in Ta ble 1. As imilar trend can also be seen when comparing the deviation of the dicyanovinyl groups relative to the central ring of the acene skeleton, namely,t he tilt angles (Table 1): 1a (g 1 = 31.5, 37.98)a nd 1c (g 1 = 34.58)v ersus TCAQ (g 1 = 34.78; g 2 = 34.18), [35] TCTQ (g 1 = 38.88), [50] and 6,13-TCPQ (g 1 = 39.68; g 2 = 39.18). [50] UV/Vis analysis TCPQ derivativesa re typicallyc olorless or yellow,a nd they feature absorptions in the UV or high-energyv isible regions.…”

“…[24] First reported in 1960 by Acker et al, [25,26] pristine TCNQ has become one of the most extensively studied acceptor materials. [24,32,[35][36][37][38] It was originally expected that exTCNQs could offer more stable and improvedc onducting materials. [24,32,[35][36][37][38] It was originally expected that exTCNQs could offer more stable and improvedc onducting materials.…”

Directly-linked intramolecular donor–acceptor compounds of ferrocene and tetracyanoanthraquinodimethane

“…The infrared spectra of 1 and 2 each show the m(CN) stretching frequency at 2222 cm À1 , not significantly different from the parent TCNAQ [21][22][23]. The m(CN) stretching frequencies of polycyano acceptor molecules are typically sensitive to the charge on the molecule, due to the population of the out-of plane antibonding p-orbital.…”

Synthesis and characterization of conjugated polymer based on tetracyano-anthraquinodimethane

“…However, the number of acceptor units with suitable energy levels, reactivity and solubility is still limited. 11,11,12,12-Tetracyano-9,10-anthraquinodimethane (TCAQ) is a strong electron acceptor [6][7][8][9]. The TCAQ derivatives have been studied as second-order and third-order nonlinear optical (NLO) materials [10], and as p-extended electron acceptors in charge-transfer (CT) complex for many years [6][7][8].…”

“…11,11,12,12-Tetracyano-9,10-anthraquinodimethane (TCAQ) is a strong electron acceptor [6][7][8][9]. The TCAQ derivatives have been studied as second-order and third-order nonlinear optical (NLO) materials [10], and as p-extended electron acceptors in charge-transfer (CT) complex for many years [6][7][8]. Donor/acceptor-conjugated polymers based on TCAQs could have strong intra-molecular donor-acceptor interactions and low LUMO energy levels, and might result in useful materials for optoelectronic applications.…”