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Keywords = quantum yield (TPE)

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14 pages, 2472 KiB  
Article
Role of Substitution Patterns in Four Regioisomeric Tetraphenylethylene–Thiophene Derivatives
by Shuai Hou, Hanxiao Tian, Ruiyao Li, Zishuai Huang, Dongyuan Zhu, Fan Xiao, Yunmeng Zhao and Jingjing Xu
Molecules 2025, 30(14), 2953; https://doi.org/10.3390/molecules30142953 - 13 Jul 2025
Viewed by 430
Abstract
Tetraphenylethylene (TPE)–thiophene compounds are promising candidates for stimuli-responsive luminescent materials, yet systematic investigations into the influence of substitution patterns on their photophysical properties remain limited. Herein, four regioisomeric TPE–thiophene derivatives have been synthesized by systematically varying the number and positions of TPE substituents [...] Read more.
Tetraphenylethylene (TPE)–thiophene compounds are promising candidates for stimuli-responsive luminescent materials, yet systematic investigations into the influence of substitution patterns on their photophysical properties remain limited. Herein, four regioisomeric TPE–thiophene derivatives have been synthesized by systematically varying the number and positions of TPE substituents on the thiophene core. A comprehensive spectroscopic characterization reveals that substitution patterns critically modulate the photoluminescence quantum yields (PLQYs). The ortho-monosubstituted isomer exhibits the highest PLQY (52.86% in solid state) compared with the meta-monosubstituted isomer (13.87% in solid state). Interestingly, thiophenes with two or three TPEs substituted at positions 2,5 or 2,3,5 have lower PLQYs, which is rare due to the common understanding that increasing the number of AIE parts should increase the PLQY. Further single-crystal structure analyses show that the key factor impacting the PLQY is the dihedral angles of the TPE subunit, which determines the degree of intramolecular twisting. This work establishes regiochemistry as a powerful design lever for tuning TPE–thiophene photophysics, offering underlying principles for the design of TPE-based thiophene molecules with high photoluminescent performance in the future. Full article
(This article belongs to the Special Issue Photochemistry in Asia)
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35 pages, 20847 KiB  
Review
The ATTO 565 Dye and Its Applications in Microscopy
by Yuheng Wu and René M. Williams
Molecules 2024, 29(17), 4243; https://doi.org/10.3390/molecules29174243 - 6 Sep 2024
Viewed by 1789
Abstract
ATTO 565, a Rhodamine-type dye, has garnered significant attention due to its remarkable optical properties, such as a high fluorescence quantum yield, and the fact that it is a relatively stable structure and has low biotoxicity. ATTO 565 has found extensive applications in [...] Read more.
ATTO 565, a Rhodamine-type dye, has garnered significant attention due to its remarkable optical properties, such as a high fluorescence quantum yield, and the fact that it is a relatively stable structure and has low biotoxicity. ATTO 565 has found extensive applications in combination with microscopy technology. In this review, the chemical and optical properties of ATTO 565 are introduced, along with the principles behind them. The functionality of ATTO 565 in confocal microscopy, stimulated emission depletion (STED) microscopy, single-molecule tracking (SMT) techniques, two-photon excitation–stimulated emission depletion microscopy (TPE-STED) and fluorescence correlation spectroscopy (FCS) is discussed. These studies demonstrate that ATTO 565 plays a crucial role in areas such as biological imaging and single-molecule localization, thus warranting further in-depth investigations. Finally, we present some prospects and concepts for the future applications of ATTO 565 in the fields of biocompatibility and metal ion detection. This review does not include theoretical calculations for the ATTO 565 molecule. Full article
(This article belongs to the Special Issue Advances in Functional Organic Dye Chemistry)
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12 pages, 4258 KiB  
Article
Improving the Electroluminescence Properties of New Chrysene Derivatives with High Color Purity for Deep-Blue OLEDs
by Sunwoo Park, Changyu Lee, Hayoon Lee, Kiho Lee, Hyukmin Kwon, Sangwook Park and Jongwook Park
Materials 2024, 17(8), 1887; https://doi.org/10.3390/ma17081887 - 19 Apr 2024
Viewed by 1628
Abstract
Two blue-emitting materials, 4-(12-([1,1′:3′,1″-terphenyl]-5′-yl)chrysen-6-yl)-N,N-diphenylaniline (TPA-C-TP) and 6-([1,1′:3′,1″-terphenyl]-5′-yl)-12-(4-(1,2,2-triphenylvinyl)phenyl)chrysene (TPE-C-TP), were prepared with the composition of a chrysene core moiety and terphenyl (TP), triphenyl amine (TPA), and tetraphenylethylene (TPE) moieties as side groups. The maximum photoluminescence (PL) emission wavelengths of TPA-C-TP and TPE-C-TP were 435 [...] Read more.
Two blue-emitting materials, 4-(12-([1,1′:3′,1″-terphenyl]-5′-yl)chrysen-6-yl)-N,N-diphenylaniline (TPA-C-TP) and 6-([1,1′:3′,1″-terphenyl]-5′-yl)-12-(4-(1,2,2-triphenylvinyl)phenyl)chrysene (TPE-C-TP), were prepared with the composition of a chrysene core moiety and terphenyl (TP), triphenyl amine (TPA), and tetraphenylethylene (TPE) moieties as side groups. The maximum photoluminescence (PL) emission wavelengths of TPA-C-TP and TPE-C-TP were 435 and 369 nm in the solution state and 444 and 471 nm in the film state. TPA-C-TP effectively prevented intermolecular packing through the introduction of TPA, a bulky aromatic amine group, and it showed an excellent photoluminescence quantum yield (PLQY) of 86% in the film state. TPE-C-TP exhibited aggregation-induced emission; the PLQY increased dramatically from 0.1% to 78% from the solution state to the film state. The two synthesized materials had excellent thermal stability, with a high decomposition temperature exceeding 460 °C. The two compounds were used as emitting layers in a non-doped device. The TPA-C-TP device achieved excellent electroluminescence (EL) performance, with Commission Internationale de L′Eclairage co-ordinates of (0.15, 0.07) and an external quantum efficiency of 4.13%, corresponding to an EL peak wavelength of 439 nm. Full article
(This article belongs to the Special Issue The 15th Anniversary of Materials—Recent Advances in Materials Chemistry)
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12 pages, 1821 KiB  
Article
Effect of Polymer Composition on the Optical Properties of a New Aggregation-Induced Emission Fluorophore: A Combined Experimental and Computational Approach
by Alberto Picchi, Qinfan Wang, Francesco Ventura, Cosimo Micheletti, Jesse Heijkoop, Francesco Picchioni, Ilaria Ciofini, Carlo Adamo and Andrea Pucci
Polymers 2023, 15(17), 3530; https://doi.org/10.3390/polym15173530 - 24 Aug 2023
Viewed by 2285
Abstract
Nowadays, fluorophores with a tetraphenylethylene (TPE) core are considered interesting due to the aggregation-induced emission (AIE) behavior that enables their effective use in polymer films. We propose a novel TPE fluorophore (TPE-BPAN) bearing two dimethylamino push and a 4-biphenylacetonitrile pull moieties [...] Read more.
Nowadays, fluorophores with a tetraphenylethylene (TPE) core are considered interesting due to the aggregation-induced emission (AIE) behavior that enables their effective use in polymer films. We propose a novel TPE fluorophore (TPE-BPAN) bearing two dimethylamino push and a 4-biphenylacetonitrile pull moieties with the typical AIE characteristics in solution and in the solid state, as rationalized by DFT calculations. Five different host polymer matrices with different polarity have been selected: two homopolymers of poly(methylmethacrylate) (PMMA) and poly(cyclohexyl methacrylate) (PCHMA) and three copolymers at different compositions (P(MMA-co-CHMA) 75:25, 50:50, and 25:75 mol%). The less polar comonomer of CHMA appeared to enhance TPE-BPAN emission with the highest quantum yield (QY) of about 40% measured in P(MMA-co-CHMA) 75:25. Further reduction in polymer polarity lowered QY and decreased the film stability and adhesion to the glass surface. LSC performances were not significantly affected by the matrix’s polarity and resulted in around one-third of the state-of-the-art due to the reduced QY of TPE-BPAN. The theoretical investigation based on density functional theory (DFT) calculations clarified the origin of the observed AIE and the role played by the environment in modulating the photophysical behavior. Full article
(This article belongs to the Special Issue Advanced Spectroscopy Methods in Polymer-Based Materials Analysis and Characterization)
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12 pages, 1822 KiB  
Article
Two-Photon–Near Infrared-II Antimicrobial Graphene-Nanoagent for Ultraviolet–Near Infrared Imaging and Photoinactivation
by Wen-Shuo Kuo, Yen-Sung Lin, Ping-Ching Wu, Chia-Yuan Chang, Jiu-Yao Wang, Pei-Chi Chen, Miao-Hsi Hsieh, Hui-Fang Kao, Sheng-Han Lin and Chan-Chi Chang
Int. J. Mol. Sci. 2022, 23(6), 3230; https://doi.org/10.3390/ijms23063230 - 17 Mar 2022
Cited by 4 | Viewed by 2502
Abstract
Nitrogen doping and amino group functionalization through chemical modification lead to strong electron donation. Applying these processes to a large π-conjugated system of graphene quantum dot (GQD)-based materials as electron donors increases the charge transfer efficiency of nitrogen-doped amino acid-functionalized GQDs (amino-N-GQDs), [...] Read more.
Nitrogen doping and amino group functionalization through chemical modification lead to strong electron donation. Applying these processes to a large π-conjugated system of graphene quantum dot (GQD)-based materials as electron donors increases the charge transfer efficiency of nitrogen-doped amino acid-functionalized GQDs (amino-N-GQDs), resulting in enhanced two-photon absorption, post-two-photon excitation (TPE) stability, TPE cross-sections, and two-photon luminescence through the radiative pathway when the lifetime decreases and the quantum yield increases. Additionally, it leads to the generation of reactive oxygen species through two-photon photodynamic therapy (PDT). The sorted amino-N-GQDs prepared in this study exhibited excitation-wavelength-independent two-photon luminescence in the near-infrared region through TPE in the near-infrared-II region. The increase in size resulted in size-dependent photochemical and electrochemical efficacy, increased photoluminescence quantum yield, and efficient two-photon PDT. Therefore, the sorted amino-N-GQDs can be applicable as two-photon contrast probes to track and localize analytes in in-depth two-photon imaging executed in a biological environment along with two-photon PDT to eliminate infectious or multidrug-resistant microbes. Full article
(This article belongs to the Special Issue Carbon-Based Nanomaterials 3.0)
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