Aggregation-induced emission and solid fluorescence of fluorescein derivatives

Feng, Shumin; Gong, Shengyi

doi:10.1039/c9cc09784h

Cited by 46 publications

(52 citation statements)

References 16 publications

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“…While the tails do not directly influence the energy ordering of excited states, they maye nhancen on-radiativep athways due to the increased conformational flexibility. [11a, 19] Ar ecent report on fluo- rescein derivatives found that increasing the alkyl sidechain length reduced QY of the monomeric state, [20] whereas conformationall ocking typically increases the QY for conjugated chromophores. [11a, 21] Notably,x ylindein thin films exhibit relativelyh igh electron mobility as shown by the I-V curvest aken in the dark (Figure S10a), [6b] corroborating the p-p stacking and H-bonding network betweena djacent xylindein molecules (see above).…”

mentioning

confidence: 99%

Ultrafast Dynamics and Photoresponse of a Fungi‐Derived Pigment Xylindein from Solution to Thin Films

Krueger

Giesbers

Court³

et al. 2021

Chemistry A European J

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Organics emiconductor materials have recently gained momentum due to their non-toxicity,l ow cost, and sustainability.X ylindein is ar emarkably photostable pigment secreted by fungi that grow on decaying wood, and its relativelys trong electronic performance is enabled by p-p stacking and hydrogen-bonding network that promote charget ransport. Herein, femtosecondt ransienta bsorption spectroscopy with an ear-IRp robe was used to unveil ar apid excited-state intramolecular protont ransfer reaction. Conformational motions potentially lead to a conical intersection that quenches fluorescence in the monomeric state. In concentrated solutions, nascent aggregates exhibit af aster excited state lifetime due to excimer formation, confirmed by the excimer!charge-transfer excited-state absorption band of the xylindein thin film, thus limiting its optoelectronic performance. Therefore, extending the xylindein sidechains with branched alkyl groups mayh indert he excimer formation and improve optoelectronic properties of naturally derived materials.

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mentioning

confidence: 99%

Ultrafast Dynamics and Photoresponse of a Fungi‐Derived Pigment Xylindein from Solution to Thin Films

Krueger

Giesbers

Court³

et al. 2021

Chemistry A European J

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“…As expected for AIE undergoing molecules, the aggregation process involving the self-assembly of emissive units improve fluorescence. Hydrogen bonding and van der Waals interactions are involved in the process [71]. On solutions of NBDF probe was observed the typical behaviour of AIEgens, depending on a different solvent/non-solvent ratio.…”

Section: Spectroscopic Behaviormentioning

confidence: 92%

Section: Spectroscopic Behaviormentioning

confidence: 99%

A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

et al. 2020

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We developed a new benzodifuran derivative as the condensation product between 2,6-diamino -4-(4-nitrophenyl)benzo [1,2-b:4,5-b']difuran-3,7-dicarboxylate and 3-hydroxy-2-naphthaldehyde. The intramolecular hydrogen-bond interactions in the terminal half-salen moieties produce a sterically encumbered highly conjugated main plane and a D-A-D (donor-acceptor-donor) T-shaped structure. The novel AIEgen (aggregation-induced enhanced emission generator) fulfils the requirement of RIR (restriction of intramolecular rotation) molecules. DR/NIR (deep red/near infrared) emission was recorded in solution and in the solid state, with a noteworthy photoluminescence quantum yield recorded on the neat crystals which undergo some mechanochromism. The crystal structure study of the probe from data collected at a synchrotron X-ray source shows a main aromatic plane π-stacked in a columnar arrangement.Crystals 2020, 10, 269 2 of 15 law [20][21][22] the intrinsic low band-gap of such DR/NIR emitters makes them especially vulnerable to the ACQ effect [23] due to higher vibrionic coupling between the ground and excited states. Therefore, most of the AIEgens reported emit blue and green lights. Although they are highly sought after for red OLEDs (Organic Light Emitting Diodes), night-vision devices, secured displays, optical waveguides and in the wide field of bio and chemo-sensing [24][25][26][27][28], there are fewer efficient DR/NIR (deep red/near infrared) materials. Of particular interest are AIE fluorophores with intense emission at DR/NIR region owing to their deep tissue penetration, photo-stability and minimum interference in living systems [25,29,30]. Their applications are closely related to cell imaging and DNA and protein sensing [31][32][33].Novel molecular construction of DR/NIR AIEgens can be achieved with electron donor (D) and electron acceptor (A) blocks connected through π-conjugated frameworks. The most fundamental phenomenon governing the spectroscopic properties is the intramolecular charge transfer (ICT) process from the donor to the acceptor in the excited state [34][35][36]. Intercrossed excited state between the low-lying local exciton (LE) and charge transfer (CT) exciton results from the D-A interaction. Obviously, the molecular geometry is crucial for the process.Benzodifuran derivatives have drawn attention for a wide range of biological and pharmacological applications, including antimicrobial, antiviral, analgesic and antitumor [37][38][39][40] activity. This class of heterocyclic compounds are also employed in dyes industry as pigments and in different fields of optoelectronics and photonics. Due to the excellent semiconducting properties [41,42], benzodifuran scaffolds are used as nonlinear optical materials [43], for dye sensitized solar cells [44] and in organic solar cell and transistors. Finally, as electron-rich building blocks they have a potential in the constructing of photoluminescent materials [45][46][47] Herein, we developed a new benzodifuran derivative from 2,6-diamino-4-(4-nitrophenyl) ...

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“…Fluorescein presents also a weak Stokes shift, the interval between highest absorption and emission wavelength, which is a potential issue for devices using a single optical path, such as entry-level plate readers. Like most intense fluorescent probes, self-quenching can occur in case of aggregation (ACQ) or high degrees of surface substitution [25]. Hopefully, due to low the concentration used in biological systems, this drawback has little relevance.…”

Section: Fluorescein: Synthesis and Propertiesmentioning

confidence: 99%

Fluorescein Derivatives as Fluorescent Probes for pH Monitoring along Recent Biological Applications

Guern

Mussard

Gaucher

et al. 2020

IJMS

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Potential of hydrogen (pH) is one of the most relevant parameters characterizing aqueous solutions. In biology, pH is intrinsically linked to cellular life since all metabolic pathways are implicated into ionic flows. In that way, determination of local pH offers a unique and major opportunity to increase our understanding of biological systems. Whereas the most common technique to obtain these data in analytical chemistry is to directly measure potential between two electrodes, in biological systems, this information has to be recovered in-situ without any physical interaction. Based on their non-invasive optical properties, fluorescent pH-sensitive probe are pertinent tools to develop. One of the most notorious pH-sensitive probes is fluorescein. In addition to excellent photophysical properties, this fluorophore presents a pH-sensitivity around neutral and physiologic domains. This review intends to shed new light on the recent use of fluorescein as pH-sensitive probes for biological applications, including targeted probes for specific imaging, flexible monitoring of bacterial growth, and biomedical applications.

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Aggregation-induced emission and solid fluorescence of fluorescein derivatives

Abstract: The AIE and strong solid fluorescence of fluorescein derivatives can be realized in a simple way.

Cited by 46 publications

References 16 publications

Ultrafast Dynamics and Photoresponse of a Fungi‐Derived Pigment Xylindein from Solution to Thin Films

Ultrafast Dynamics and Photoresponse of a Fungi‐Derived Pigment Xylindein from Solution to Thin Films

A Novel DR/NIR T-Shaped AIEgen: Synthesis and X-Ray Crystal Structure Study

Fluorescein Derivatives as Fluorescent Probes for pH Monitoring along Recent Biological Applications

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