A New Series of C‐6 Unsubstituted Tetrahydropyrimidines: Convenient One‐Pot Chemoselective Synthesis, Aggregation‐Induced and Size‐Independent Emission Characteristics

Zhu, Qiuhua; Huang, Lan; Chen, Zhipeng; Zheng, Sichao; Lv, Longyun; Zhu, Zhibo; Cao, Derong; Jiang, Huanfeng; Liu, Shuwen

doi:10.1002/chem.201203012

Cited by 57 publications

(51 citation statements)

References 168 publications

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“…It has been reported that some synthetic non‐aromatic macromolecules, such as poly[(maleic anhydride)‐ alt ‐(vinyl acetate)] and vinyl polymers carrying succinic anhydride terminal groups, are also highly luminescent. Apart from these big macromolecules, some small molecules without classical chromophores have been found to show AIE activity . Zhu et al, for example, have synthesized a class of tetrahydropyrimidine derivatives with AIE characteristics .…”

Section: Structure Diversificationmentioning

confidence: 99%

“…Apart from these big macromolecules, some small molecules without classical chromophores have been found to show AIE activity . Zhu et al, for example, have synthesized a class of tetrahydropyrimidine derivatives with AIE characteristics . Luminogen 47 , for instance, is non‐emissive in solutions but becomes highly luminescent when aggregated.…”

Section: Structure Diversificationmentioning

confidence: 99%

Section: Structure Diversificationmentioning

confidence: 99%

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Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

et al. 2014

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"United we stand, divided we fall."--Aesop. Aggregation-induced emission (AIE) refers to a photophysical phenomenon shown by a group of luminogenic materials that are non-emissive when they are dissolved in good solvents as molecules but become highly luminescent when they are clustered in poor solvents or solid state as aggregates. In this Review we summarize the recent progresses made in the area of AIE research. We conduct mechanistic analyses of the AIE processes, unify the restriction of intramolecular motions (RIM) as the main cause for the AIE effects, and derive RIM-based molecular engineering strategies for the design of new AIE luminogens (AIEgens). Typical examples of the newly developed AIEgens and their high-tech applications as optoelectronic materials, chemical sensors and biomedical probes are presented and discussed.

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Section: Structure Diversificationmentioning

confidence: 99%

Section: Structure Diversificationmentioning

confidence: 99%

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Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

et al. 2014

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“…If the fluorescence changes are very sharp and visible about/at CMC, the CMC values will be directly observed. In 2011 [18], we developed an efficient five-component reaction for the synthesis of a novel series of C6-unsubstituted tetrahydropyrimidines (THPs) with strong aggregation-induced emission (AIE) characteristics, that is, no emission in solution but strong fluorescence in aggregates. AIE characteristic, found and termed by Tang's group [19], resolves the thorny aggregation-caused quenching problem of conventional fluorophores and has shown great advantages in wide areas [20], such as AIEgens-containing copolymers and their applications [21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Influence factors on the critical micelle concentration determination using pyrene as a probe and a simple method of preparing samples

Liang

et al. 2020

R. Soc. open sci.

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Zhu Q. 2020 Influence factors on the critical micelle concentration determination using pyrene as a probe and a simple method of preparing samples. R. Soc. open sci. 7: 192092. http://dx.The critical micelle concentration (CMC) is an important parameter of widely used surfactants and needs to be measured in the application and development of surfactants. Fluorometric method is a widely used method determining CMC values owing to the advantages of highly sensitivity, fast response and wide application range. There are two common methods (I and II) of preparing samples for CMC fluorometric determination. In the process of developing CMC probes with aggregation-induced emission (AIE) characteristics, we found that methods I and II were not suitable for CMC probes with AIE charateristics and developed a new sample preparation method (III), which is not only suitable for CMC probes with AIE characteristic but also decreases operation procedures and errors owing to omitting the addition of micro amount of dyes into each sample. To ascertain if method III is also suitable for other CMC probes without AIE characteristics, the CMC values of surfactants were determined by fluorometric method using widely used pyrene without AIE charateristic as probe and methods I-III to prepare samples. The obtained experimental results proved that method III not only was suitable for preparation of samples for CMC determination of surfactants using pyrene as probe but also led to the least average deviation (methods I-III led to ±0.13, ±0.34 and ±0.05 mM deviation for the CMC determination of sodium dodecyl sulfate (SDS), respectively). The CMC determination using pyrene as probe is based on its change in the ratio (I FIII /I FI ) of its emission peaks I and III with surfactant concentration. Unexpectedly, it was found that the I FIII /I FI value of pyrene in surfactant solutions is sensitive to the measurement conditions changing exciting light energy, such as slit widths and sample-measured number. In addition, it was found that surfactant SDS or cetrimonium bromide from different suppliers not only has significantly different CMC values but also leads to very different I FIII /I FI values of pyrene in a certain concentration of surfactant, which can be used as a simple method to distinguish the same surfactant with different CMC values.

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“…This view is also supported by more recent work of Zhu et al., who have examined a large series of tetrahydropyrimidines in which N‐1 has both alkyl and 4‐substituted aryl groups. They found that both types of substituents resulted in H‐6a/H‐6b geminal coupling constants in the range of −17.6 to −18.0 Hz …”

Section: Resultsmentioning

confidence: 99%

Unusually large scalar coupling between geminal protons in a saturated pyrimidine

Mazzola

Gutiérrez

Fraenkel

et al. 2016

Concepts Magnetic Resonance

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An unusually large geminal coupling has been observed in a stereochemically rigid system that permits a favorable coupling alignment between the methylene protons and an adjacent carbon-carbon double bond. Such couplings have been found to depend on both the alignment of a line connecting the geminal hydrogens and the nodal plane of the adjacent double bond, and the orientation of lone-pair electrons on adjacent heteroatoms. Electron withdrawal from symmetrical bonding orbitals results in more slightly positive geminal coupling constants while that from antisymmetrical bonding orbitals produces more negative coupling constants, which has been found to be very large in certain rigid systems. K E Y W O R D S 1 H-1 H geminal couplings, sp n hybridization, density functional theory calculations, double-bond nodal plane, hybridization, tetrahydropyrimidines

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A New Series of C‐6 Unsubstituted Tetrahydropyrimidines: Convenient One‐Pot Chemoselective Synthesis, Aggregation‐Induced and Size‐Independent Emission Characteristics

Cited by 57 publications

References 168 publications

Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

Aggregation‐Induced Emission: The Whole Is More Brilliant than the Parts

Influence factors on the critical micelle concentration determination using pyrene as a probe and a simple method of preparing samples

Unusually large scalar coupling between geminal protons in a saturated pyrimidine

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