Understanding Charge-Transfer Interaction Mode in Cocrystals and Solvates of 1-Phenyl-3-(pyren-1-yl) Prop-2-en-1-one and TCNQ

Abstract

Three binary charge-transfer cocrystals (I, II, and III) and ten cocrystal solvates (IV(1)−IV(10)) were prepared in different solvents, involving 1-phenyl-3-(pyren-1-yl) prop-2-en-1-one (PPPO) as electron donor (D) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) as electron acceptor (A). X-ray diffraction data, vibrational spectroscopy, thermal behaviors, and diffuse reflectance absorption spectroscopy were exploited to investigate their structures. The different charge-transfer interaction mode and molar ratio between donor and acceptor in these crystals can be affected by the change of solvents. In addition, PPPO and TCNQ can selectively accommodate aromatic solvents relative to other solvents except methanol to form an isostructural microporous framework with solvent residing in the channels. These results demonstrate that these crystals can have potential applications in purification and separation of aromatic hydrocarbons.

Charge-Transfer Complexes of Benzothienobenzothiophene with Tetracyanoquinodimethane and the n-Channel Organic Field-Effect Transistors

“…Recently, perylene has been reported to form not only 1:1 but also 2:1 and 3:1 TCNQ complexes, and these mixed-stack complexes show respectively electron, ambipolar, and hole-transporting transistor properties . Accordingly, similar CT complexes have been attracting considerable attention. − …”

Understanding charge transfer stacking mode in cocrystals involving Tetrachloro‐p‐benzoquinone via experimental (SXRD, DSC‐TGA, DRS) studies and hirshfeld surfaces analysis

“…1‐acetyl‐3‐phenyl‐5‐(1‐pyrenyl)‐pyrazoline (APPP), 1‐(5‐(anthracen‐9‐yl)‐3‐(4‐methoxyphen‐yl)‐4, 5‐dihydropyrazol‐1‐yl) ethanone (AMPE) and PPPO were synthesized according to the procedure previously reported in our laboratory . Tetrachloro‐p‐benzoquinone (TCQ, CAS 118‐75‐2) was purchased from Alfa and used without further purification.…”

Solvent-tuned charge-transfer properties of chiral Pt(ii) complex and TCNQ˙− anion adducts

“…In the above studies, (À)-1/(+)-1 cations and TCNQc À anions can form CT adducts, as evidenced by the crystal structure; also, the powders with different colors obtained in MeOH and H 2 O suggest that the solvent is essential in inducing polymorphism with variable CT properties. 63,64 The solvent-tuned spectroscopic variances in (À)-1-TCNQ will be investigated in the following discussion. The parent compound (À)-1 is reported to show characteristic intraligand (IL) transitions (3 > 10 4 L mol À1 cm À1 ) in the region of 200-310 nm, and metal-to-ligand charge transfer (MLCT) mixed with ligand-to-ligand charge transfer (LLCT) transitions (3 > 10 3 L mol À1 cm À1 ) in the region of 330-450 nm in MeOH solution (Fig.…”