Effect of alkyl groups on emission properties of aggregation induced emission active N-alkyl arylaminomaleimide dyes

Imoto, Hiroaki; Nohmi, Katsuya; Kizaki, Kohei; Watase, Seiji; Matsukawa, Kimihiro; Yamamoto, S.; Mitsuishi, Masaya; Naka, Kensuke

doi:10.1039/c5ra18690k

Cited by 27 publications

(16 citation statements)

References 53 publications

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“…One promising strategy for obtaining solid‐state luminescent organic materials is to construct materials based on “element‐blocks”, which are defined as a minimum functional units composed of heteroatoms . In particular, by employing boron “element‐blocks” with AIE properties, a wide variety of optically functional materials have been developed . In addition to these luminescent boron complexes, it has also been reported that several compounds containing boron exhibit solid‐state emission without bulky substituents , .…”

Section: Introductionmentioning

confidence: 99%

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

2017

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Mechanochromic luminescent molecules often suffer from critical loss of luminescence intensity during phase transitions in the solid state. In this study, we present mechanochromic luminescent molecules that can provide clear color changes with constant emission intensity during phase transitions. It was reported that the class of aggregation‐induced emission (AIE)‐active boron complexes can present intense emission by freezing intramolecular motions. According to this mechanism, we designed a complex with a fused ligand to preserve the enhanced emission in the aggregated state in the AIE during phase transitions between the solution, amorphous, and crystalline states. From optical measurements, it was shown that the synthesized boron complexes present bright emission in various phases. In particular, as we expected, the luminescence color was clearly altered during phase transition, whereas the emission intensity changed only slightly. Finally, we also found that diverse luminescence colors were obtained from each polymorph and for various substituents as induced by the substituent effect. The results in the series of mechanistic studies show that electronic interactions and π–π interactions can modulate the electronic conjugation system of the complexes without causing loss of emission efficiency.

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Section: Introductionmentioning

confidence: 99%

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

2017

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“…Among reported organic dyes, maleimide-based fluorophores, one of the smallest fluorophores, exhibit promising properties, such as high emissivity, large Stokes shifts, and ease of modification. 8 – 13 …”

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confidence: 99%

“…Despite the recent advances in this field, there has been little work on varying the maleimide structures and studying the subsequent impact on their fluorescence. 8 – 13 , 21 , 34 , 35 The search for a versatile maleimide fluorophore is pivotal in this area, where structures with well-defined reactivities and varying fluorescent profiles are needed. In this work, we systemically expanded the scope of substitution patterns, through single or double substitution reactions from halogen precursors for the first time.…”

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confidence: 99%

Rational design of substituted maleimide dyes with tunable fluorescence and solvafluorochromism

et al. 2018

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“…These moieties have large Stokes shifts ( ca 100 nm) and show solvent‐dependent emission wavelengths and intensities, with polar protic solvents causing a red shift and large reduction in emission intensity. In parallel with DTMs, they are also quenched by direct conjugation of aromatic amines to the maleimide ring, but these arylaminomaleimides have been shown to exhibit aggregation‐induced fluorescence in the solid state . We proposed, based on bromomaleimide conjugations with cysteine, that a conjugation‐induced fluorescence technique could be realized utilizing lysine residues.…”

Section: Introductionmentioning

confidence: 99%

Utilizing functionalized bromomaleimides for fluorogenic conjugation and PEGylation of enzymes

Husband

Hill

O’Reilly

2019

Polymer International

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Two efficient enzyme conjugation techniques have been explored by exploiting the reactions of bromomaleimides. The conjugations utilize monobromo-and dibromomaleimides, which have been reacted with reduced disulfide bonds or terminal amines in -chymotrypsin and human lysozyme. These reactions allow the formation of dithio-, monoamino-and aminobromomaleimides, which are solvent-dependent fluorophores and have a handle for further functionalization, which allowed fluorogenic PEGylation via this technique. In this work, the efficiency of these maleimide conjugations was monitored and the fluorescence of the resulting conjugates was examined. The quantum yields of the small-molecule maleimide conjugates were calculated, but are low due to solvent quenching effects. Catalytic activities of the conjugate enzymes were compared to those of their respective native enzymes, which show no discernible effect of the modifications on enzymatic activity or stability at room temperature.

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Effect of alkyl groups on emission properties of aggregation induced emission active N-alkyl arylaminomaleimide dyes

Abstract: Aggregation induced emission (AIE) active N-alkyl aminomaleimide dyes with various kinds of N-alkyl groups were synthesized in a one pot process.

Cited by 27 publications

References 53 publications

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

Design and Luminescence Chromism of Fused Boron Complexes Having Constant Emission Efficiencies in Solution and in the Amorphous and Crystalline States

Rational design of substituted maleimide dyes with tunable fluorescence and solvafluorochromism

Utilizing functionalized bromomaleimides for fluorogenic conjugation and PEGylation of enzymes

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