Multiple–color AIE coumarin–based Schiff bases and potential application in yellow OLEDs

Yan, Liqiang; Li, Renjie; Shen, Wei; Qi, Zhengjian

doi:10.1016/j.jlumin.2017.10.032

Cited by 69 publications

(37 citation statements)

References 42 publications

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“…The strong intermolecular interactions and perfect molecular packing could rigidify the fluorophore in the crystal lattice and lead to aggregation enhanced emission in the solid state. To further substantiate the role of molecular conformation and packing, we have compared Schiff base structures that showed strong solid statefluorescence . (2‐((2‐ hydroxybenzylidine)amino) phenoxy) benzonitrile and 2‐(4‐((2‐hydroxy‐4‐methoxy benzylidine) amino)phenoxy) benzonitrile Schiff base molecules that showed strong solid state fluorescence displayed coplanar conformation and strong π…π interactions in the crystal lattice.…”

Section: Resultsmentioning

confidence: 99%

“…(2‐((2‐ hydroxybenzylidine)amino) phenoxy) benzonitrile and 2‐(4‐((2‐hydroxy‐4‐methoxy benzylidine) amino)phenoxy) benzonitrile Schiff base molecules that showed strong solid state fluorescence displayed coplanar conformation and strong π…π interactions in the crystal lattice. 43 Other Schiff base molecules that showed strong solid state fluorescence also revealed more coplanar conformation between imine phenyl and hydroxy phenyl groups as well as strong π…π interactions in the crystal lattice . Thus molecular conformation and packing induced AEE might also plays significant role along with ESIPT for exhibiting solid state fluorescence in the family of Schiff base molecules.…”

Section: Resultsmentioning

confidence: 99%

“…Polymorph structure dependent yellow and orange AEE was observed with (E)‐4‐chloro‐2‐(((4‐(dimethylamino)phenyl)imino)methyl) phenol . Coumarin–based Schiff base derivatives displayed multiple color AEE depend on the substitution . Recently, we have reported stimuli‐responsive high‐contrast reversible fluorescence switching and nanofabrication induced white light emission via ESIPT in simple aryl‐ether based Schiff bases ,.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Kundu

Karthikeyan²,

Moon

et al. 2018

ChemistrySelect

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Excited state intramolecular proton transfer (ESIPT) materials are highly desirable because of their unique solid state fluorescence. Schiff base molecules with appropriate hydrogen donor functional group forms intramolecular H‐bonding, a basis for ESIPT, however, only few molecules show solid state fluorescence. Herein, carbazole based Schiff base molecules 1 (2‐((E)‐(4‐(9H‐carbazol‐9‐yl)phenyl‐mino)methyl)phenol), 2 (2‐((E)‐(4‐(9H‐carbazol‐9‐yl)phenylimino) methyl)‐5‐methoxyphenol), 3 (2‐((E)‐(4‐(9H‐carbazol‐9‐yl)phenyl‐imino)methyl)‐5‐(diethylamino)phenol) and 4 (1‐((E)‐(4‐(9H‐carbazol‐9‐yl)phenylimino)methyl)naphthalen‐2‐ol)) were synthesized and ESIPT induced solid state fluorescence were correlated with solid state structural conformation and molecular packing. 2 and 4 exhibited solid state fluorescence whereas 1 and 3 did not show any fluorescence even though both 1 and 3 showed strong intramolecular H‐bonding. Further structural comparison revealed that not only the intramolecular H‐bonding facilitated ESIPT, the molecular conformation and resulting molecular packing also plays important role on the solid state fluorescence. Computational studies have also been performed to get the insight on the role of molecular conformation and organization. The non‐planar twisted molecular conformation of 2 and 4 showed reversible mechanofluorochromism (MFC). Powder X‐ray diffraction indicates that hard crushing converted crystalline to amorphous/partial amorphous phase whereas heating converts amorphous to crystalline. Thus the present study provides a structural insight for developing ESIPT based new Schiff base materials.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Kundu

Karthikeyan²,

Moon

et al. 2018

ChemistrySelect

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“…Integration of AEE or halochromic functionality along with ESIPT unit produced stimuli‐responsive reversible fluorescence switching . Schiff base molecules with the ability of exhibiting imine to amine tautomer can also exhibit ESIPT induced solid state fluorescence . The strong intramolecular H‐bonding in Schiff bases produce aggregation dependent tunable as well as white fluorescence .…”

Section: Introductionmentioning

confidence: 99%

“…Schiff base molecules with the ability of exhibiting imine to amine tautomer can also exhibit ESIPT induced solid state fluorescence . The strong intramolecular H‐bonding in Schiff bases produce aggregation dependent tunable as well as white fluorescence . For Schiff bases, along with intramolecular H‐bonding the molecular conformation also plays important role for making them to solid state fluorescence .…”

Section: Introductionmentioning

confidence: 99%

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing

et al. 2020

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Schiff base molecules of 1–4 ((E)‐N′‐benzylidene‐2‐hydroxybenzohydrazide derivatives) showed structure controlled solid state fluorescence tuning, reversible stimuli induced fluorescence switching and highly selective Co2+ sensing. The strong intramolecular H‐bonding between imine and amine facilitates excited state intramolecular proton transfer (ESIPT) and large red shifted solid state fluorescence. Positional isomers and substitutional change tuned the solid state fluorescence (460 to 605 nm). The substituents and positions control stimuli‐induced fluorescence switching. ESIPT fluorophores showed strong fluorescence in DMF (Φf=0.057 to 0.35 compared to quinine sulphate). ESIPT fluorophores (2–4) exhibited highly selective fluorescence sensing of Co2+ ions without significant interference from other metal ions. Concentration dependent studies of fluorophores show the detection limit (LOD) of 54 nM that is much lower than the Environmental Protection Agency (EPA) guideline value (1.7 μM) in drinking water. Solid state fluorescence of ESIPT fluorophores have been made use to fabricate solid fluorescence assay (PVA polymer composite thin films) and demonstrated highly selective fluorescence sensing of Co2+ upon dipping into aqueous metal ions solution. Thus, the present studies demonstrate the versatility of Schiff base molecules for developing ESIPT fluorophores for stimuli responsive materials and highly selective fluorescence sensing both in solution and solid state.

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Solid‐state emissive biphenylene bridged bisaroyl‐S,N‐ketene acetals as distinct aggregation‐induced enhanced emitters and fluorometric probes

Biesen

Müller

2021

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Biphenylene bridged bisaroyl-S,N-ketene acetals can be readily synthesized by a one-pot Masuda borylation-Suzuki arylation sequence, thus, yielding a library of 20 bisaroyl-S,N-ketene acetals with tunable solid-state emission and aggregationinduced enhanced emission characteristics depending on the para substituents in the starting material. Potential applications as fluorometric probe of alcoholic beverages are outlined.

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Multiple–color AIE coumarin–based Schiff bases and potential application in yellow OLEDs

Cited by 69 publications

References 42 publications

Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing

Solid‐state emissive biphenylene bridged bisaroyl‐S,N‐ketene acetals as distinct aggregation‐induced enhanced emitters and fluorometric probes

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Multiple–color AIE coumarin–based Schiff bases and potential application in yellow OLEDs

Cited by 69 publications

References 42 publications

Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Molecular Conformation‐ and Packing‐Controlled Excited State Intramolecular Proton Transfer Induced Solid‐State Fluorescence and Reversible Mechanofluorochromism

Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co2+ Fluorescence Sensing

Solid‐state emissive biphenylene bridged bisaroyl‐S,N‐ketene acetals as distinct aggregation‐induced enhanced emitters and fluorometric probes

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Easily Accessible Schiff Base ESIPT Molecules with Tunable Solid State Fluorescence: Mechanofluorochromism and Highly Selective Co²⁺ Fluorescence Sensing