Single‐Benzene Fluorophores: Controlling Electron Density on Amino of 2,5‐Diaminoterephthalates to Manipulate Optical/Electronic Properties for Efficient and Diversified Functions DOI
Zhiwei Bao,

Yuchen Yang,

Xiaoqian Wu

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: 34(40)

Published: May 15, 2024

Abstract Single‐benzene fluorophores have attracted increasing interest owing to their simple molecular structure and unique photophysical properties. Developing novel single‐benzene with facile synthesis, bright tunable dual‐state emissions, diversified functions is highly desirable. Herein, a strategy of controlling electron density on amino 2,5‐diaminoterephthalates proposed modulate emission, acidichromism, Cu 2+ detection, lipid droplets (LDs) staining. A series efficient based 2,5‐diaminoterephthalate skeleton emissions in blue red region large Stokes shifts facilely developed. The obtained various substituents groups exhibit different acidichromism property. Two (ABB ABM) high sensitivity selectivity toward detection ratiometric “turn‐off” fluorescence mechanism for ABM ABB, respectively. limit determined be 1.40 × 10 −7 4.35 −9 mol L −1 ABB ABM, Moreover, three (ABT, green emission display superior LDs‐targeting capability specificity, brightness. This design philosophy provides new way designing practical applications.

Language: Английский

Precise Manipulation of Excited-State Intramolecular Proton Transfer via Incorporating Charge Transfer toward High-Performance Film-Based Fluorescence Sensing DOI
Ke Liu, Jing Zhang,

Qiyuan Shi

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(13), P. 7408 - 7415

Published: March 17, 2023

Excited-state intramolecular proton transfer (ESIPT) has been widely employed for the design of a variety functionality-led molecular systems. However, precise manipulation excited-state reaction is challenging. Herein, we report new tactic tuning ESIPT via incorporating an charge (ESICT) process. Specifically, three o-carborane derivatives, NaCBO, PaCBO, and PyCBO, were designed, where 2-(2'-hydroxyphenyl)-benzothiazole typical unit functioning as electron acceptor, electron-donating units are naphthyl-(Na), phenanthrenyl-(Pa), pyrenyl-(Py), respectively. The architectures molecules featured with face-to-face alignment two units. Spectroscopy theoretical calculation studies revealed that capacity donors solvent polarity continuously modulate ESIPT/ESICT energetics dynamics, resulting in distinct emissions. Moreover, depicted not only highly porous structures but also very different fluorescent colors solid state, enabling selective film-based fluorescence sensing mustard gas simulant, 2-chloroethyl ethyl sulfide, detection limit 50 ppb response time 5 s. This work thus provides reliable strategy creation high-performance fluorophores manipulation.

Language: Английский

Citations

80
Excited-State Intramolecular Proton Transfer (ESIPT) Based Metal–Organic Supramolecular Optical Materials: Energy Transfer Mechanism and Luminescence Regulation Strategy DOI

Peng‐Yan Fu,

Shao‐Zhe Yi,

Mei Pan

et al.

Accounts of Materials Research, Journal Year: 2023, Volume and Issue: 4(11), P. 939 - 952

Published: Oct. 3, 2023

ConspectusDuring the past few years, excited-state intramolecular proton transfer (ESIPT) has attracted great attention in field of metal–organic optical materials due to their rich photophysical properties. Generally, ESIPT process includes unique four-leveled photocycle and concomitant multiemissions, leading complex luminescence mechanisms variable phenomena. In contrast with widely reported research on pure organic photoluminescent molecules, aid modern techniques such as situ X-ray diffraction transient study, supramolecular are emerging recent which have adjustable frame structures, diverse emission types, excellent performance. Through regulating equilibrium transformation relationship various processes (nonradiative transitions, radiative energy transfer, charge etc.), ESIPT-based demonstrate wide applications displaying, sensing, imaging, lasing, etc. Given that deep understanding properties is still its infancy, numerous new strategies for need be established urgently. this short Account, we describe a construction regulation system materials, including four types levels conversion, corresponding photoluminescence (PL) strategies, potential application demonstrations.Based our work related reports from other groups, Account proposes synthesize regulate PL Namely, can described ESIPT-process-directed enol/keto strategy, ISC (intersystem crossing)/RISC (reverse intersystem crossing)-process-directed fluorescence/persistent metal-centered (MC) monomer/excimer respectively. It should noted first two implemented small molecule they enhanced optimized based ligand-centered (LC) emission, while last systems. We will shed light between regulated by process.Collectively, above approaches propose illustrated basic mechanism specific examples (for elaboration some also included) Account. anticipate principles used better utilization construct materials. And further envisaged, paving way future design more advanced

Language: Английский

Citations

28
Hydrogen-Bonded Thiol Undergoes Unconventional Excited-State Intramolecular Proton-Transfer Reactions DOI Creative Commons
J.-K. Wang, Chih‐Hsing Wang,

Chi-Chi Wu

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(5), P. 3125 - 3135

Published: Jan. 30, 2024

The chapter on the thiol-related hydrogen bond (H-bond) and its excited-state intramolecular proton-transfer (ESIPT) reaction was recently opened where compound 4'-diethylamino-3-mercaptoflavone (

Language: Английский

Citations

17
A Fluorescent Probe with Zwitterionic ESIPT Feature for Ratiometric Monitoring of Peroxynitrite In Vitro and In Vivo DOI
Zhen‐Kai Wang, Miao Yan, Miaomiao Yu

et al.

Analytical Chemistry, Journal Year: 2024, Volume and Issue: 96(8), P. 3600 - 3608

Published: Feb. 19, 2024

Peroxynitrite (ONOO–), as a short-term reactive biological oxidant, could lead to series of effects in various physiological and pathological processes due its subtle concentration changes. In vivo monitoring ONOO– relevant is urgently required. Herein, we describe novel fluorescent probe termed HBT-Fl-BnB for the ratiometric detection vitro vivo. The consists an HBT core with Fl groups at ortho para positions responding zwitterionic excited-state intramolecular proton-transfer (zwitterionic ESIPT) process boronic acid pinacol ester dual roles that block ESIPT recognize ONOO–. Thanks specificity well low cytotoxicity, success imaging endogenous exogenous living cells by was obtained. Additionally, applicability tracking abnormal expression induced inactivated Escherichia coli also explored. This first report sensing via mechanism.

Language: Английский

Citations

17
Impact of Host–Emitter Interactions on Light Amplification in Laser Dyes DOI Creative Commons
Masashi Mamada,

Ayano Abe,

Takashi Fujihara

et al.

Aggregate, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

ABSTRACT Organic lasers hold great promise for enabling a new class of future optoelectronics. Consequently, the development organic semiconductors as gain media has recently been subject significant interest. The molecular design principle based on Einstein coefficients validated achieving high gain, with para ‐phenylene‐vinylene scaffolds recognized one most crucial frameworks. In this study, we develop stilbene tetramer derivative, QSBCz, which significantly increased conjugation compared to highly efficient laser material, BSBCz, resulting in remarkably radiative decay rate and large cross‐section. However, find that optical losses play role light amplification QSBCz. Indeed, comprehensive understanding suppression detrimental loss pathways throughout lasing process are essential, whereas intrinsically associated molecules have not well considered. Although host–guest systems helpful preventing concentration quenching aggregated states, study reveals notable when using common host such 4,4′‐bis(9 H ‐carbazol‐9‐yl)biphenyl (CBP) mCBP. contrast, BSBCz derivative is successfully employed host, leading improved stimulated emission amplification. These findings indicate importance host–emitter interactions properties highlight necessity optimize materials developing dyes.

Language: Английский

Citations

1
A Materials Acceleration Platform for Organic Laser Discovery DOI Creative Commons
Tony Wu, Andrés Aguilar-Gránda, Kazuhiro Hotta

et al.

Advanced Materials, Journal Year: 2022, Volume and Issue: 35(6)

Published: Nov. 14, 2022

Conventional materials discovery is a laborious and time-consuming process that can take decades from initial conception of the material to commercialization. Recent developments in acceleration platforms promise accelerate using automation experiments coupled with machine learning. However, most efforts chemistry focus on synthesis compound identification, integrated target property characterization receiving less attention. In this work, an automated platform introduced for molecules as gain mediums organic semiconductor lasers, problem has been challenging conventional approaches. This encompasses lego-like synthesis, product optical be executed fully end-to-end fashion. Using workflow screen laser candidates, discovered eight potential candidates lasers discovered. The lasing threshold four thin-film devices find two state-of-the-art performance tested. These promising results show screening accelerated development.

Language: Английский

Citations

35
Fluorescence emission mechanism for the π-conjugated zwitterion 2,4-Bisimidazolylphenol base on ESIPT: A TDDFT theoretical reconsideration DOI
Yan Lu,

Meilin Guo,

Yu Wan

et al.

Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy, Journal Year: 2024, Volume and Issue: 312, P. 124043 - 124043

Published: Feb. 14, 2024

Language: Английский

Citations

9
Tuning Molecular Packing by Twisting Structure to Facilely Construct Highly Efficient Solid‐State Fluorophores for Two‐Photon Bioimaging and Photodynamic Therapy DOI
Hui Cao, Ya Gao,

Bingshun Wu

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: 34(27)

Published: March 7, 2024

Abstract The traditional design strategy for constructing highly bright solid‐state luminescent materials relies on incorporating aggregation‐induced emission (AIE) scaffolds, molecular rotors, or bulky substituents to prevent close cofacial packing, which limits the diversity in developing new materials. Herein, a of tuning packing by twisting structure conventional aggregation‐caused quenching fluorophore is proposed endow with AIE effect and enhance fluorescence. Accordingly, series 1,4‐bis(diphenylamino)‐2,5‐disubstituted benzene fluorophores exhibiting characteristics, high fluorescence efficiency (up 0.99), wide color tunability, good near‐infrared (NIR) two‐photon absorption facilely developed. All these luminogens can specifically stain intracellular lipid droplets signal‐to‐noise ratio, biocompatibility, photostability. Besides, exhibit effective reactive oxygen species (ROS) generation capability upon low‐power white light irradiation. Among them, luminogen, named BDBDC, integrating NIR emission, strongest ROS demonstrates superior performances imaging various tissues photodynamic cancer therapy. This philosophy provides way designing practical applications.

Language: Английский

Citations

9
Multi-Emission Carbon Dots Combining Turn-On Sensing and Fluorescence Quenching Exhibit Ultrahigh Selectivity for Mercury in Real Water Samples DOI

Panpan Zhu,

Sheng‐Li Hou, Zhenhai Liu

et al.

Environmental Science & Technology, Journal Year: 2024, Volume and Issue: 58(22), P. 9887 - 9895

Published: May 22, 2024

Mercury is a ubiquitous heavy-metal pollutant and poses serious ecological human-health risks. There an ever-growing demand for rapid, sensitive, selective detection of mercury in natural waters, particularly regions lacking infrastructure specialized analysis. Here, we show that sensor based on multi-emission carbon dots (M-CDs) exhibits ultrahigh sensing selectivity toward Hg(II) complex environmental matrices, tested the presence range environmentally relevant metal/metalloid ions as well artificial ligands, using various real water samples. By incorporating structural features calcein folic acid enable tunable emissions, M-CDs couple emission enhancement at 432 nm simultaneous reduction 521 nm, with intensity ratio linearly related to concentration up 1200 μg/L, independent matrix compositions. The have limit 5.6 response time 1 min, spike recovery 94 ± 3.7%. intensified attributed proton transfer aggregation-induced enhancement, whereas quenching due electron transfer. These findings also important implications identification other matrices routine, screening-level food safety health management practices.

Language: Английский

Citations

7
Precise Electron-Withdrawing Strength Modulation of ESIPT Probes for Ultrasensitive and Specific Fluorescence Sensing DOI

Yanwen Guo,

Zhenzhen Cai,

Fei Yan

et al.

Analytical Chemistry, Journal Year: 2023, Volume and Issue: 95(23), P. 9014 - 9024

Published: June 1, 2023

The precise regulation of the electron-withdrawing/electron-donating strength in a probe is great significance for design reaction-based fluorescent probes with specific functionalities. Here, family excited-state intramolecular proton transfer (ESIPT)-based fluorescence turn-on sensing properties toward KMnO4 was designed by precisely modulating electron-withdrawing substituents located at para-position recognition group. It found that −F, −CHO, and −H as groups bound can specifically recognize KMnO4, which ensures blue emission displayed reaction products. Especially −CHO group, product shows most stable fluorescence. 2-(benzo[d]oxazol-2-yl)-4-formylphenyl acrylate (BOPA-CHO) demonstrated more superior performance including low limit detection (LOD, 0.96 nM), rapid response (<3 s), rather good selectivity even presence 21 interferents. Moreover, practicality further verified test pen comprising BOPA-CHO-embedded sponge, capable detecting solid naked-eye LOD 11.62 ng. present modulation strategy would open up new path high-performance probes.

Language: Английский

Citations

15