Aggregation-enhanced emission in fluorophores containing pyridine and triphenylamine terminals: restricted molecular rotation and hydrogen-bond interaction

Deng, Shiang-Lin; Chen, Tai-Lin; Chien, Wei-Lun; Hong, Jin‐Long

doi:10.1039/c3tc31592d

Cited by 55 publications

(26 citation statements)

References 27 publications

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“…Solvents were dried by recommended procedures and distilled under an inert atmosphere prior to use. The starting materials 4‐(diphenylamino)benzaldehyde ( 4 a ) and 4‐(bis(4‐methoxyphenyl)amino)benzaldehyde ( 4 b ), and reference osmanapthalyne complex 1′ were prepared by procedures described in the literature. Other reagents, including ferrocene, decamethylferrocene, and cobaltocene, that were used in the electrochemical studies, were received from commercial suppliers and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Zhang

Jin

et al. 2018

Chemistry A European J

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Diarylamine‐substituted osmanaphthalyne complexes that feature two redox centers linked by the rigid skeleton of the metallacycle (C^C+), specifically, [OsCl2(PPh3)2{(C^C+)NAr2}][BF4−] (Ar=Ph (1 a), p‐MeOPh (1 b)) and their open‐ring precursors [OsHCl2(PPh3)2{(≡C−C(PPh3+)=CHPh)NR2}][BF4−] (Ar=Ph (2 a), p‐MeOPh (2 b)), were successfully synthesized and characterized by 1H, 13C, and 31P NMR spectroscopy, ESI‐MS, and elemental analysis. The solid‐state molecular structures of complexes 1 a and 2 a were ascertained by single‐crystal X‐ray diffraction. The Os≡C bond length in both complexes 1 a and 2 a fell within the range reported for similar osmanaphthalynes and osmium carbyne complexes, respectively. The structural parameters determined for complex 1 a, which were successfully reproduced by theoretical calculations, point to a π‐delocalized metallacycle structure. The purple color of compounds 1 a and b was explained by the diarylamine→Os(metallacycle) charge‐transfer absorption in the visible region. The neutral, one‐electron‐oxidized and one‐electron‐reduced states of compounds 1 a, b, and a reference complex that lacked the diarylamine substituent, [OsCl2(PPh3)2{(C^C+)}][BF4−] (1′), were investigated by cyclic and square‐wave voltammetry, UV/Vis/NIR spectroelectrochemistry, and DFT calculations. The spin density in singly oxidized complexes [1 a]+ and [1 b]+ predominantly resided on the aminyl segment, with osmium involvement controlled by the diphenylamine substitution. Spin density in stable, singly‐reduced [1′]− was distributed mainly over the osmanaphthalyne metallacycle.

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Section: Methodsmentioning

confidence: 99%

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Zhang

Jin

et al. 2018

Chemistry A European J

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“…The annealed film shown in Figure 4 was slightly greener than the initial film and the written character with further grinding was less obvious (see Figure S2, Supporting Information). It can be presumed that part of the well‐ground T4 powder introduced into the polymer matrix formed hydrogen bonds with PVA upon annealing 18…”

Section: Resultsmentioning

confidence: 99%

“…It can be presumed that part of the well-ground T4 powder introduced into the polymer matrix formed hydrogen bonds with PVA upon annealing. [18] 2. Study of the MCL mechanism -effects of the nitrogen position…”

Section: Mechanochromic Photoluminescencementioning

confidence: 99%

Mechanochromic Luminescence Characteristics of Pyridine‐Terminated Chromophores in the Solid State and in a Poly(vinyl alcohol) Matrix

Kondo

Miura

Okumoto

et al. 2014

Chemistry An Asian Journal

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Mechanoresponsive luminophores containing different substituted pyridine rings at the molecular terminus are synthesized and their photoluminescence properties are investigated. The solid chromophore with a 4-substituted pyridine ring exhibits a reversible photoluminescent color change, while the 2-substituted chromophore shows only a small change in luminescence, and the 3-substituted chromophore displays an irreversible photoluminescent color change with mechanical grinding. A change of the sample color in response to mechanical grinding is also achieved for a dye-dispersed poly(vinyl alcohol) film. Furthermore, a simultaneous acid and mechanoresponsive photoemission color change is achieved in the dye-dispersed film.

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“…Organic molecules which are non‐emissive in the molecularly dissolved state but strongly emit light in the aggregate form (achieved by addition of poor solvent or analyte complexation), are known as AIEgens. Up to now, AIEgens’ family includes siloles, tetraphenylethenes, salicylaldehyde azines, pyrrole and diketopyrrolopyrroles, cyanostilbenes, pyrazine,diphenyldibenzofulvenes, and other derivatives . The AIE fluorophores are beneficial in the fields of organic light emitting diode (OLED), cell staining and drug delivery by virtue of high emission in the solid state and in aqueous environment .…”

Section: Introductionmentioning

confidence: 99%

Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

Singh

Vanita

et al. 2016

ChemistrySelect

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Here in, we report self‐assembled aggregates of AIEgen 1, which exhibits excited state intramolecular proton transfer (ESIPT) coupled aggregation induced emission (AIE) with intense green fluorescence (λem=526 nm) in aqueous solution as well as in solid state. AIEgen 1 behaves as disassembly based fluorescent probe for selective and sensitive detection of Cu2+ in drinking water with lowest limit of detection of 0.261 ppb (4.13 nM) (much lower than recommended by EPA). AIEgen 1 finds applications for the detection of Cu2+ in blood serum, environmental (tap, pond and industrial waste water) samples. Probably the interaction of Cu2+ ions at Schiff‐base unit of AIEgen 1 via metal chelation disrupts the self‐assembled aggregates and results in disassembly of the nanorods into smaller spherical nanostructures as also evidenced in DLS, SEM and TEM studies. Incubation of HeLa cells with AIEgen 1 results in fluorescence ‘switch‐on’ showing cell internalization of AIEgen 1 with low cytotoxicity and thus establishes the potential of AIEgen 1 in cell imaging. The reversibility influorescence / absorbance of 1‐Cu2+ complex with EDTA helps in elaboration of various reconfigurable and superposed logic gates such as NOT (at F425, A380), INH (at A430), IMP1 (at A380) and IMP2 (at F526). By observing the output switching in absorbance and fluorescence channels on addition of Cu2+ (In1) and EDTA (In2) as inputs, ‘set‐ reset’ flip flop memory element and complementary IMP/INH logic circuits have been elaborated.

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Aggregation-enhanced emission in fluorophores containing pyridine and triphenylamine terminals: restricted molecular rotation and hydrogen-bond interaction

Cited by 55 publications

References 27 publications

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Mechanochromic Luminescence Characteristics of Pyridine‐Terminated Chromophores in the Solid State and in a Poly(vinyl alcohol) Matrix

Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

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Aggregation-enhanced emission in fluorophores containing pyridine and triphenylamine terminals: restricted molecular rotation and hydrogen-bond interaction

Cited by 55 publications

References 27 publications

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Diphenylamine‐Substituted Osmanaphthalyne Complexes: Structural, Bonding, and Redox Properties of Unusual Donor–Bridge–Acceptor Systems

Mechanochromic Luminescence Characteristics of Pyridine‐Terminated Chromophores in the Solid State and in a Poly(vinyl alcohol) Matrix

Nanomolar Cu2+Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits

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Product

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Nanomolar Cu²⁺Detection in Water Based on Disassembly of AIEgen: Applications in Blood Serum, Cell Imaging and Complex Logic Circuits