Regulation of circular dichroism behavior and construction of tunable solid-state circularly polarized luminescence based on BINOL derivatives

Zhao, Na; Gao, Wangwang; Zhang, Min; Yang, Jiaxin; Zheng, Xiaoyan; Li, Yue; Cui, Rongrong; Yin, Wei; Li, Nan

doi:10.1039/c9qm00292h

Cited by 30 publications

(32 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although AIEgens are potentially useful agents for bioimaging, they must be biocompatible for any potential biological application. Hence, the in vitro biocompatibility of S4 was evaluated in mouse fibroblast cells L929 [49] . The details of the experimental procedures are provided in the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly,t he luminogens S3 and S4 displayed dissimilar aggregation-induced CD signals.A sa lready reportedi nt he literature, [49,50] the reduction of the CD signal is generally ac onsequence of the decrease in the torsiona ngle between the adjacent naphthalener ings of (R)-BINOL. Therefore, it is reasoned that the corresponding torsion angle in S3 has reduced in the aggregated state, observed beyond4 0% water addition.…”

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 94%

“…Thus, the close proximity of the -CN groups to the phenyl ring allows as trongeri nteraction than is the case for -C=Oi nS3, thereby enhancingt he torsiona ngle. [49,50] The overlay of the energy-minimised structures of the luminogens S3 and S4 shows ag reater dihedral angle between the naphthyl rings of the (R)-BINOLi nS4 arising from steric hindrance ( Figure 13). Thereby,asmalls tructuralm odification can result in the inversion of aggregation-induced CD behaviour in the designed molecules, and this provides us with ah andle to tune the chiroptical properties of the molecules.…”

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 99%

“…Hence, the in vitro biocompatibility of S4 wase valuated in mouse fibroblast cells L929. [49] The detailso ft he experimental procedures are provided in the Supporting Information. Resorufin, ab lue-coloured non-fluorescent dye, wasu sed to quantify the percentage cell viability and it was found that S4 is highly biocompatiblew ith these cells at concentrationsi nt he range 10-100 mgmL À1 (with ca.…”

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 99%

See 3 more Smart Citations

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

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 94%

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 99%

Section: Circular Dichroism Spectra Of S3 and S4mentioning

confidence: 99%

See 2 more Smart Citations

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

View full text Add to dashboard Cite

show abstract

“…Li and co‐workers, [ 48 ] by inserting various bridged alkyl chains into the hydroxyl groups of 3,30‐dicyanomethylene functionalized ( R )‐BINOL, synthesized a series of chiral luminogens ( R )‐13 ( n = 1–8) and compounds 14 ( n = 6 with substituents with markedly different electronic characteristics). All 13 exhibited AIE behavior and their molecular conformation was significantly dependent on the length of the alkyl chain, which further regulated their CD response from annihilation to preservation in the aggregated state.…”

Section: Discussionmentioning

confidence: 99%

Aggregation‐Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies

2020

View full text Add to dashboard Cite

physical property differentiating two enantiomers is the direction of rotation of the polarized light. Indeed, the manipulation of polarized light, both in the absorbance and emission mode, is useful in a series of technological applications, such as liquid crystal display (LCD) panels, 3D imaging in biological systems, nonlinear optics, spintronic devices. [5-8] Progresses in the field have been boosted by the increased availability of modern spectroscopic methods. For circular dichroism (CD), which relates to ground-state properties, the commercial availability of the spectrophotometer dates back to the 1960s and has enabled in depth studies of the tertiary structure of proteins. In contrast, circularly polarized luminescence (CPL) spectrophotometers have only been recently commercially available. Nevertheless, CPL gives important additional informations, as it provides information on the excited-state, and luminescence is generally more of interest in terms of materials science and devices. [9] Emissive organic materials have been studied for decades. Among these, organic light-emitting diodes (OLEDs) have reached large-scale commercialization, since they show unique technological advantages with respect to previous technologies: energy-saving, low working voltage, high brightness, and contrast display. Polarized emission and CPL has been the subject of increasing interest. Indeed, circularly polarized OLEDs (CP-OLEDs), based on chiral organic chromophores, have been realized and reported in the recent literature. A variety of chiral organic emitters have been proposed for CPL materials. [10] Aggregation-caused quenching (ACQ) of emission is a common problem that can severely limit the performance of (chiral and achiral) fluorophores in the solid state. The field of emissive dyes has been revolutionized in the early 2000s by Tang's group, which introduced the concept, seemingly counterintuitive at the time, of aggregation-induced emission (AIE). Suitable AIE chromophores (AIEgens) can exhibit strong fluorescence emission in aggregated states, despite being nonemissive in solution. [11] The most frequent mechanism for AIE occurs when AIEgens have freely-rotating groups which, upon excitation, relax back through these rotations instead of releasing energy as light. When they aggregate or crystallize, they become emissive through restricted intramolecular rotation (RIR). Since then, the AIE field literally exploded, and several reports have started to appear on chirality-related CPL emissive dyes. [12] Chirality is becoming increasingly important in the design of organic materials with functional properties, when bulk anisotropy is needed. In the past decades, a plethora of chiral organic materials have been studied and developed. Nanostructures have brought substantial advancement to the realization of organic-molecule-based devices, and the possibilities for solid-state light emission are very promising in view of potential applications. Scientific approaches to the realization of chiral emissive materials are ...

show abstract

Circularly Polarized Luminescence of Aggregation‐induced Emission Materials

Gan

Shen

Qiu

2022

Handbook of Aggregation‐Induced Emission

View full text Add to dashboard Cite

Regulation of circular dichroism behavior and construction of tunable solid-state circularly polarized luminescence based on BINOL derivatives

Abstract: Circular dichroism behavior was regulated by controlling the molecular conformation of BINOL derivatives, and tunable solid-state circularly polarized luminescence was achieved.

Cited by 30 publications

References 62 publications

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

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

Aggregation‐Induced Circularly Polarized Luminescence: Chiral Organic Materials for Emerging Optical Technologies

Circularly Polarized Luminescence of Aggregation‐induced Emission Materials

Contact Info

Product

Resources

About