Cocrystal Assembled by Pyrene Derivative and 1,4-Diiodotetrafluorobenzene via a C=O···I Halogen Bond

Abstract

Cocrystal formation is a strategy used to modify the solid-state properties of a given molecule. In this study, a new cocrystal assembled by 1,4-Diiodotetrafluorobenzene (1,4-DITFB) and a pyrene derivative, 1-acetyl-3-phenyl-5-(1-pyrenyl)-pyrazoline (APPP), was synthesized. Due to the twisted structure of APPP, the crystal structure is greatly different with some large π-conjugated compounds, which exhibits edge-to-face π-stacked arrangement between 1,4-DITFB and pyrene rings, rather than the face-to-face π-stacked arrangement. Hirshfeld surface analysis and the shift of characteristic vibration band of the carbonyl group in FT-IR spectroscopy suggest the formation of a C=O···I halogen bond.

Ionic-Liquid-Assisted One-Step Construction of Mesoporous Metal–Organic Frameworks

“…Additionally, the in-plane wobble peak of −(CH 2 ) 2 – of the alkyl chain was detected at 809 cm –1 . The conjugation effect generated by the presence of the aromatic group makes the CO peak at 1690 cm –1 in MIL-101 shift to 1659 cm –1 in MIL-101-Phe . When the IL content was increased from 0 to 2:1 (the molar ratio of IL/TPA), regardless of whether it was for MIL-101-Phe or MIL-101-HPy (Figure b), the crystalline form of Fm 3 m (the MIL-101 cell parameters) remained unchanged, showing that the immobilization of ILs did not damage MIL-101’s crystal structure.…”

“…The conjugation effect generated by the presence of the aromatic group makes the C�O peak at 1690 cm −1 in MIL-101 shift to 1659 cm −1 in MIL-101-Phe. 50 When the IL content was increased from 0 to 2:1 (the molar ratio of IL/TPA), The stable framework structure of MIL-101 was used in combination with ILs as secondary ligands in an attempt to increase the size of the pores produced by the framework synthesis process from micro-to meso-sized pores. According to Figure 7a, the N 2 adsorption−desorption isotherms of MIL-101-Phe and MIL-101-HPy (Figure 7a) displayed a type IV isotherm with an H2-type hysteresis loop, which is indicative of a mesoporous material with uniform pore size 51 and is incompatible with the structure of MIL-101.…”

The Stoichiometry of TCNQ-Based Organic Charge-Transfer Cocrystals

“…There are many papers related to charge transfer cocrystals published in several special issues of the journal Crystals covering different aspects, including donor-acceptor packing type of co-crystals [43,44], hydrogen-bonded co-crystals [45,46], conducting and superconducting co-crystals [47,48], etc. However, it is still worth discussing the role of stoichiometry between donor and acceptor in co-crystals.…”

Assembling photoactive materials from polycyclic aromatic hydrocarbons (PAHs): room temperature phosphorescence and excimer-emission in co-crystals with 1,4-diiodotetrafluorobenzene

“…[52][53][54][55] In this context, co-crystallization of luminescent molecules proved to be a powerful tool for developing new materials and achieving emission type and color fine-tuning. 48,[56][57][58][59][60][61] The type of co-formers to be used in co-crystallization with PAHs is rather limited, as hydrocarbons do not possess typical hydrogen bonding groups. Suitable systems are perfluoropolyhalogenated molecules, since they can drive cocrystallization by establishing halogen bonding interactions of the type X⋯π with the electron density of the aromatic rings in PAH molecules.…”