Interactions between haloperfluorobenzenes and fluoranthene in luminescent cocrystals from π-hole⋯π to σ-hole⋯π bonds

Abstract

From π-hole⋯π to σ-hole⋯π bonds between haloperfluorobenzenes and fluoranthene in luminescent cocrystals.

Cocrystals with tunable luminescence colour self-assembled by a predictable method

“…With the above considerations in mind, five haloperfluorobenzenes, namely octafluoronaphthalene (C10F8), 1,4-dibromotetrafluorobenzene (14DBrPB), 1,4-diiodotetrafluorobenzene (14DIPB), 1,3,5-tribromo-2,4,6-trifluorobenzene (TBrPB) and 1,3,5-trifluoro-2,4,6-triiodobenzene (TIPB), were chosen as the -hole bonding or -hole bonding donors which assemble cocrystals with acenaphthene (AC) as the bonding acceptor. The molecular SEPs of selected molecules are calculated to predict the bonding patterns between AC and five bonding donors (Li et al, 2017). The results of XRD analysis show that the main bonding pattern in AC-C10F8/14DBrPB/TBrPB cocrystals is a -holeÁ Á Á bond, whereas a -holeÁ Á Á bond is the major the bonding pattern in AC-14DIPB/TIPB.…”

Organic Cocrystals: Beyond Electrical Conductivities and Field‐Effect Transistors (FETs)

“…[1] When 1,3,5-trifluoro-2,4,6-triiodobenzene (IFB) and 1,4-diiodotetrafluorobenzene (F4DIB) are selected as acceptors,asegregated stacking form with charge-transfer interactions or am ixed stacking form without charge-transfer interactions are obtained ( Figure 4, DD' and DB'). [21,67] Compared with the single-component DPO crystals,t he resulting DPO-based co-crystals exhibit tunable optical properties and multi-color polarized emission within the UV/blue region, and also present reversible mechanochromic fluorescence (MCF) properties.T hese new properties make DPO-based co-crystals candidates for applications in solid UV/blue opto-electronics.Non-or poor fluorescent 3ring-N-heterocyclic hydrocarbons ( Figure 4, VB',W B ',X B ', SB',TB',UB, and TP') [68][69][70][71] and fluoranthene ( Figure 4, KD', KK',KP',and KN') [72] in the solid-state can be endowed with different emissions,s uch as pink, orange,o range yellow, green, or blue light after being co-crystalized with haloperfluorobenzenes.T he emitting colors of (naphthylvinyl)pyridine can also be adjusted via co-crystallizing with HFB or 4bromo-2,3,5,6-tetrafluorobenzoic acid (Figure 4, EB' and EI'). [21,67] Compared with the single-component DPO crystals,t he resulting DPO-based co-crystals exhibit tunable optical properties and multi-color polarized emission within the UV/blue region, and also present reversible mechanochromic fluorescence (MCF) properties.T hese new properties make DPO-based co-crystals candidates for applications in solid UV/blue opto-electronics.Non-or poor fluorescent 3ring-N-heterocyclic hydrocarbons ( Figure 4, VB',W B ',X B ', SB',TB',UB, and TP') [68][69][70][71] and fluoranthene ( Figure 4, KD', KK',KP',and KN') [72] in the solid-state can be endowed with different emissions,s uch as pink, orange,o range yellow, green, or blue light after being co-crystalized with haloperfluorobenzenes.T he emitting colors of (naphthylvinyl)pyridine can also be adjusted via co-crystallizing with HFB or 4bromo-2,3,5,6-tetrafluorobenzoic acid (Figure 4, EB' and EI').…”

“…They prepared two typical kinds of organic luminescent cocrystals with tunable emission colors and comprising pyrene-OFN and pyrene-TCNB.I nterestingly,t he cocrystals demonstrate distinct optical properties due to different intermolecular interactions,arene-perfluoroarene (AP) and charge-transfer interactions.U nexpectedly,apyrene-TCNB complex with strong charge-transfer interactions can generate WLE when doped into ap yrene-OFN host. [74], [1], [26], [4], [21], [43], [ 60], [ 25], [65], [70], [68], [ 72] and [73]. [76][77][78] Ref.…”

“…These factors make Bpe-IFB and F4DIB-IFB show different properties,f or example, strong violet-blue photoluminescence for Bpe-IFB,a nd interesting white-light emission and optical waveguide property for F4DIB-IFB.S upramolecular cocrystals of solid UV/ blue luminescent materials are also obtained based on 2,5diphenyloxazole (DPO) and four typical co-assembled coformers (4-bromotetrafluorobenzene carboxylic acid, F4DIB, OFN,a nd pentafluorophenol) ( Figure 4, RB',R G ' and KC'). [21,67] Compared with the single-component DPO crystals,t he resulting DPO-based co-crystals exhibit tunable optical properties and multi-color polarized emission within the UV/blue region, and also present reversible mechanochromic fluorescence (MCF) properties.T hese new properties make DPO-based co-crystals candidates for applications in solid UV/blue opto-electronics.Non-or poor fluorescent 3ring-N-heterocyclic hydrocarbons (Figure 4, VB',W B ',X B ', SB',TB',UB, and TP') [68][69][70][71] and fluoranthene ( Figure 4, KD', KK',KP',and KN') [72] in the solid-state can be endowed with different emissions,s uch as pink, orange,o range yellow, green, or blue light after being co-crystalized with haloperfluorobenzenes.T he emitting colors of (naphthylvinyl)pyridine can also be adjusted via co-crystallizing with HFB or 4bromo-2,3,5,6-tetrafluorobenzoic acid (Figure 4, EB' and EI'). [43] Thetwo-photon emission with adjustable wavelengths can be achieved in this way,w hich helps make the cocrystals candidates for up-conversion materials.…”

“…In these supramolecular systems,a ne fficient energy-transfer behavior from pyrene-OFN to pyrene-TCNB occurred due to the well-matched spectra of the precursors and as uitable energy D/A distance.I na ddition to above-mentioned two kinds of acceptors,t here are other acceptors that have been reported for tuning optical properties more recently. [76][77][78] [74], [1], [26], [4], [21], [43], [ 60], [ 25], [65], [70], [68], [ 72] and [73].…”