Chiral AIEgens – Chiral recognition, CPL materials and other chiral applications

Hu, Ming; Feng, Haitao; Yuan, Ying-Xue; Zheng, Yan‐Song; Tang, Ben Zhong

doi:10.1016/j.ccr.2020.213329

Cited by 228 publications

(118 citation statements)

References 159 publications

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“…Another interesting class of techniques is based on enantioselective molecular probes/sensors (5)(6)(7)(8)(9)(10)(11)(12). These methods provide only a rough estimation of the ee values, not as accurate as those determined by chiral HPLC.…”

Section: Introductionmentioning

confidence: 99%

Helical springs as a color indicator for determining chirality and enantiomeric excess

et al. 2021

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Chirality plays a key role in the physiological system, because molecular functionalities may drastically alter due to a change in chirality. We report herein a unique color indicator with a static helicity memory, which exhibits visible color changes in response to the chirality of chiral amines. A difference of less than 2% in the enantiomeric excess (ee) values causes a change in the absorption that is visible to the naked eyes. This was further quantified by digital photography by converting to RGB values. This system relies on the change in the tunable helical pitch of the π-conjugated polymer backbone in specific solvents and allows rapid on-site monitoring of chirality of nonracemic amines, including drugs, and the simultaneous quantitative determination of their ee values.

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Section: Introductionmentioning

confidence: 99%

Helical springs as a color indicator for determining chirality and enantiomeric excess

et al. 2021

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“…[12][13][14][15][16] Among the plethora of AIEgenst hat have been developed, chiralA IEgens specifically have received tremendousa ttention owingt ot heir ability to enantiodiscriminate chiral analytes. [17][18][19][20][21][22][23][24][25][26][27][28] AIE fluorophores are normally accessed by two wellrecognised approaches, either by structurallyt uning the existing AIEgenso rb ya ppending AIEgenic molecules to ACQ luminophores. Analogously,c hiral AIEgensh ave also been successfully synthesised by fusing well-knowna chiralA IEgenst oc hiral scaffolds such as sugars,a mino acids or axially chiral [1,1'-binaphthalene]-2,2'-diol (BINOL; Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Analogously,c hiral AIEgensh ave also been successfully synthesised by fusing well-knowna chiralA IEgenst oc hiral scaffolds such as sugars,a mino acids or axially chiral [1,1'-binaphthalene]-2,2'-diol (BINOL; Figure 1). [17][18][19][20][21][22][23][24][25][26][27][28] Nevertheless, designs trategies that employa mino acids and sugars lead to AIEgens with poor thermal stability that lacks cope forw avelengthtunability.B INOL, vastly explored in asymmetric catalysis [29][30][31][32][33] and bearing at remendous resemblance to the rotorlike structures of typical AIEgens such as tetraphenylethene (TPE) or tetraphenylsiloles, has been used to design chiralluminogens through the appendage of well-known AIEgensa ta ppropriate positions of BINOL ( Figure 1). [34][35][36] However, these existing design strategies are mostly limited to scaffolds such as TPE or tetraphenylsiloles.…”

Section: Introductionmentioning

confidence: 99%

Design and Development of Axially Chiral Bis(naphthofuran) Luminogens as Fluorescent Probes for Cell Imaging

Jejurkar

Yashwantrao

Kumar

et al. 2021

Chemistry A European J

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Designing chiral AIEgensw ithouta ggregation-induced emission (AIE)-active molecules externally tagged to the chiral scaffold remains al ong-standing challenge for the scientific community.T he inherenta ggregation-caused quenching phenomenon associated with the axially chiral (R)-[1,1'-binaphthalene]-2,2'-diol ((R)-BINOL)s caffold, together with its marginal Stokes shift, limits its applicationa sa chiral AIE-active material. Here, in our effort to designc hiral luminogens, we have developed ad esign strategy in which 2-substitutedf urans, when appropriately fused with the BINOLs caffold,w ill generates olid-state emissive materials with high thermala nd photostability as well as colour-tunable properties. The excellent biocompatibility,t ogetherw ith the high fluorescenceq uantum yield and large Stokes shift, of one of the luminogens stimulated us to investigate its cell-imaging potential. Thel uminogen was observedt ob e well internalised and uniformlyd ispersed within the cytoplasm of MDA-MB-231 cancer cells,s howingh ighf luorescence intensity.

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“…A new class of fluorescent materials ( Figure 1B ) with aggregation-induced emission (AIE) discovered by Tang's group and others have received considerable attention due to their unique photophysical properties (Luo et al, 2001 ; An et al, 2002 , 2012 ; Shimizu et al, 2009 ; Shustova et al, 2013 ; Yan et al, 2015 ; Sasaki et al, 2016 ; Li and Li, 2017 ; Tsujimoto et al, 2017 ; Zhang et al, 2017 ; Ren et al, 2019 ; Guo et al, 2020 ; Hu et al, 2020 ; Kong et al, 2020 ; Mao et al, 2020 ; Qin et al, 2020 ). The widely accepted working mechanism of AIE-active fluorescent materials is restriction of intramolecular motions (Mei et al, 2015 ; Chen et al, 2019 ; Tu et al, 2020 ), thus the AIE materials generally show strong emission in aggregate and solid states and strong photobleaching resistance (Hong et al, 2011 ; Chen Y. et al, 2018 ; Cao et al, 2019 ; Li et al, 2019 ; Chen et al, 2020 ; Feng H. et al, 2020 ; He et al, 2020b ; Huang et al, 2020 ; Li Q. et al, 2020 ; Ni et al, 2020 ; Wei et al, 2020 ; Xu Y. et al, 2020 ; Yin et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Fluorescent AIE-Active Materials for Two-Photon Bioimaging Applications

Lü

Liu

et al. 2020

Front. Chem.

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Fluorescence imaging has been widely used as a powerful tool for in situ and real-time visualization of important analytes and biological events in live samples with remarkably high selectivity, sensitivity, and spatial resolution. Compared with one-photon fluorescence imaging, two-photon fluorescence imaging exhibits predominant advantages of minimal photodamage to samples, deep tissue penetration, and outstanding resolution. Recently, the aggregation-induced emission (AIE) materials have become a preferred choice in two-photon fluorescence biological imaging because of its unique bright fluorescence in solid and aggregate states and strong resistance to photobleaching. In this review, we will exclusively summarize the applications of AIE-active materials in two-photon fluorescence imaging with some representative examples from four aspects: fluorescence detection, in vitro cell imaging, ex vivo tissue imaging, and in vivo vascular imaging. In addition, the current challenges and future development directions of AIE-active materials for two-photon bioimaging are briefly discussed.

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Chiral AIEgens – Chiral recognition, CPL materials and other chiral applications

Cited by 228 publications

References 159 publications

Helical springs as a color indicator for determining chirality and enantiomeric excess

Helical springs as a color indicator for determining chirality and enantiomeric excess

Design and Development of Axially Chiral Bis(naphthofuran) Luminogens as Fluorescent Probes for Cell Imaging

Fluorescent AIE-Active Materials for Two-Photon Bioimaging Applications

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