Polyimides with Heavy Halogens Exhibiting Room-Temperature Phosphorescence with Very Large Stokes Shifts

Kanosue, Kenta; Ando, Shinji

doi:10.1021/acsmacrolett.6b00642

Cited by 98 publications

(74 citation statements)

References 30 publications

(58 reference statements)

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“…Among the luminescent materials, phosphorescence materials have attracted more attention because of long triplet lifetime, large Stokes shift, high signal-to-noise ratio (Cai et al, 2018;Xie et al, 2017;An et al, 2015;Kanosue & Ando, 2016;Li et al, 2018;Zhen et al, 2017;Bolton et al, 2011;Adachi et al, 2001) and higher internal quantum efficiency of triplet excitons (Brown et al, 1993;Baldo et al, 1999; Adachi et al, ISSN 2052-5206 # 2018 International Union of Crystallography 2001). Pure organic compounds generally produce no or very weak phosphorescence, but there are some ways to strengthen their phosphorescence, such as the heavy-atom effect (Koziar & Cowan, 1978), hyperfine coupling (Kuno et al, 2015), rigidization effect (Jin et al, 1994), H-aggregation (An et al, 2015) and orbital-confinement effect (Má rquez et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

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

Liu

Wen

et al. 2018

Acta Crystallogr Sect B

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Organic light-emitting materials play an essential role in the field of luminescent materials because they are easily prepared and they have controllable luminescent properties. Here it is shown that intermolecular interactions and luminescent properties of cocrystals can be predicted using the molecular surface electrostatic potential of selected -hole/-holeÁ Á Á bonding donor haloperfluorobenzenes and acceptor acenaphthene (AC). Single-crystal X-ray diffraction data reveal that actual bonding patterns in five cocrystals assembled from haloperfluorobenzenes and AC are in accordance with predictable patterns of intermolecular interactions; that is -holeÁ Á Á bond is the major interaction in AC-octafluoronaphthalene, AC-1,4-dibromotetrafluorobenzene and AC-1,3,5-tribromo-2,4,6-trifluorobenzene cocrystals, whereas -holeÁ Á Á bond is the major interaction in AC-1,4-diiodotetrafluorobenzene and AC-1,3,5-trifluoro-2,4,6-triiodobenzene cocrystals. The luminescent properties of the cocrystals are affected by the bonding patterns between AC and haloperfluorobenzenes; the -holeÁ Á Á bond leads to weak phosphorescence, whereas the -holeÁ Á Á bond results in weak delayed fluorescence and relatively strong phosphorescence. research papers Acta Cryst. (2018). B74, 610-617 Lili Li et al. Cocrystals with tunable luminescence colour 611 research papers Acta Cryst. (2018). B74, 610-617 Lili Li et al. Cocrystals with tunable luminescence colour 617

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Section: Introductionmentioning

confidence: 99%

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

Liu

Wen

et al. 2018

Acta Crystallogr Sect B

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“…The efficient in-air RTP and the large Stokes shifts of the complexes developed are desirable properties which will be useful in development of photoluminescence materials. The Au complexes are expected to have potential applications in luminescent probes for bioimaging and for chemical sensing, and spectral conversion materials for displays, photovoltaic cells, plant cultivation, and related technologies [44][45][46][47][48][49].…”

Section: Discussionmentioning

confidence: 99%

Highly Efficient Aggregation-Induced Room-Temperature Phosphorescence with Extremely Large Stokes Shift Emitted from Trinuclear Gold(I) Complex Crystals

et al. 2019

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Highly efficient (≈75% quantum yield), aggregation-induced phosphorescence is reported. The phosphorescence is emitted at room temperature and in the presence of air from crystals of trinuclear Au(I) complexes, accompanied by an extremely large Stokes shift of 2.2 × 104 cm−1 (450 nm). The mechanism of the aggregation-induced room-temperature phosphorescence from the Au complex crystals was investigated in terms of the crystal packing structure and the primary structure of the molecules. It was found that two kinds of intermolecular interactions occurred in the crystals, and that these multiple dual-mode intermolecular interactions in the crystals play a crucial role in the in-air room-temperature phosphorescence of the trinuclear Au(I) complexes.

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“…In recent years, the incorporation of heavy bromide atom has been utilized extensively for the construction of pure organic materials with room‐temperature phosphorescence . The well‐known heavy atom effect of bromide can promote both singlet‐to‐triplet and triplet‐to‐singlet intersystem crossing by enhanced spin–orbit coupling . Furthermore, the rigidification effect of halogen bonding in solid states will suppress nonradiative relaxation of triplets, and thus strengthen the phosphorescent emission .…”

Section: Methodsmentioning

confidence: 99%

Aggregation‐Induced Emission of Highly Planar Enaminone Derivatives: Unexpected Fluorescence Enhancement by Bromine Substitution

Shu

Liu

et al. 2019

Advanced Optical Materials

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F…S, can be served as "conformational lock" to limit the free rotation of aromatic rings, which is a widely used approach to designing organic thin film transistor (OTFT) and organic photo voltaics (OPV) materials. [17][18][19] However, the planar π-conjugated molecules are always resulting fluorescence quenched in the solid state due to the tightly π-π stacking. For better application in the field of luminescence, it is urgently need to develop planar organic π-conjugated molecules with AIE-active. [20,21] For example, Yang et al. introduced S…O or Se…O noncovalent intramolecular interactions into ACQ molecules, which stabilized planar structure and restricted the photoisomerization in solid state, resulting in interesting AIE effects. [20] Halogen bonding as noncovalent interaction has been widely adopted in supramolecular chemistry for self-assembly of liquid crystals, magnetic and conducting materials and biological systems, whereas drew relatively less attention in the design of organic solid fluorescent materials. [22][23][24][25] In recent years, the incorporation of heavy bromide atom has been utilized extensively for the construction of pure organic materials with roomtemperature phosphorescence. [26][27][28] The well-known heavy atom effect of bromide can promote both singlet-to-triplet and triplet-to-singlet intersystem crossing by enhanced spin-orbit coupling. [29,30] Furthermore, the rigidification effect of halogen bonding in solid states will suppress nonradiative relaxation of triplets, and thus strengthen the phosphorescent emission. [31,32] For example, Bolton et al. revealed the importance of intermolecular short contact halogen bonding (CO⋅⋅⋅BrAr) on the bright phosphorescence from crystals or cocrystals of 2,5-dihexyloxy-4-bromobenzaldehyde and its analogs. [33] Shi et al. also demonstrated that the formation of multiple Br⋅⋅⋅Br halogen bonding in solid states could enhance phosphorescence quantum yields for a series of dibromobenzene derivatives. [34] At the same time, the heavy-atom effect always leads to significant fluorescent quenching of bromine-substituted organic fluorophores compared with their hydrogen analogs. [35,36] However, tunable multicolor solid-state fluorescence has been observed in organic cocrystals with the supramolecular arrangements governed by halogen bonding. [37] In another example, several metal-organic cages equipped with halogen bonding interactions exhibited brighter solid state emission than their organic fluorescent ligands. [38] Therefore, halogen bonding may also have a great potential for the construction of organic solid fluorescent materials.Unlike typical aggregation-induced-emission (AIE) molecules with twist/rotor structures, two AIE-active enaminone derivatives with highly planar conformations are herein reported. Interestingly, the bromine-substituted enaminone fluorophore (BrE) exhibits unexpected stronger emission in solid states than unsubstituted enaminone fluorophore (HE), which is seldom observed for organic fluorophores. Remarkably, the fluo...

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Polyimides with Heavy Halogens Exhibiting Room-Temperature Phosphorescence with Very Large Stokes Shifts

Cited by 98 publications

References 30 publications

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

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

Highly Efficient Aggregation-Induced Room-Temperature Phosphorescence with Extremely Large Stokes Shift Emitted from Trinuclear Gold(I) Complex Crystals

Aggregation‐Induced Emission of Highly Planar Enaminone Derivatives: Unexpected Fluorescence Enhancement by Bromine Substitution

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