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

Abstract

Co-crystallization between the polycyclic aromatic hydrocarbons anthracene (A) and 9-methylanthracene (MA) with 1,4-diiodotetrafluorobenzene (I2F4) afforded three novel co-crystals, viz. A∙(I2F4)2 and an unexpectedly complex system with two distinct compositions, namely...

Organic Binary and Ternary Cocrystal Engineering Based on Halogen Bonding Aimed at Room‐Temperature Phosphorescence

“…For example, 1,4-diiodotetrafluorobenzene (DITFB) and polycyclic aromatic hydrocarbons (PAHs) or their derivatives can be cocrystallized based on halogen bonding though they have different chemical structures. [14][15][16][17][18][19][20][21][22][23][24][25][26][27] DITFB is one of the common halogen bonding donors because the strong electronwithdrawing groups make positive surface regions (σ-hole and π-hole) on the molecular surface, as shown in Figure 1. [15][16][17][18] The typical acceptors in ORTP cocrystals are PAHs having a…”

Halogen bonding with carbon: directional assembly of non-derivatised aromatic carbon systems into robust supramolecular ladder architectures

“…S2†). 55 Diffraction-quality single crystals of ( anthra )( 14tfib ) 2 were obtained by dissolving the mechanochemically made material in hot CH 2 Cl 2 , rapidly cooling in an ice bath for ca. 10 seconds, followed by slow evaporation.…”

“…The structure of ( anthra )( 14tfib ) 2 was also recently reported by Azzali et al and our experimental data fully agrees with it. 55…”

Preference in the Type of Halogen Bonding Interactions within Co-Crystals of Anthraquinone with a Pair of Isosteric Perhalobenzenes

“…In comparison, the binding energy for a π-type halogen bond for both donors was also calculated in order to compare the energetic differences. In particular, a co-crystal containing C 6 I 2 F 4 and anthracene [11] was selected, along with a solid based upon C 6 I 2 Cl 4 and naphthalene [20]. Again, the DFT calculations used atomic positions from the published diffraction data.…”

“…As a result, the fluorine atoms within C 6 I 2 F 4 generate the largest positive σ-hole on the iodine atoms, making this an ideal aromatic donor. Due to this fact, C 6 I 2 F 4 has been shown to engage in both n-type [7][8][9] and π-type [10,11] halogen bonds to form numerous co-crystals or multi-component molecular solids.…”