Article
Chemistry, Multidisciplinary
Jian Zhang, Ran Zhang, Kaiqiang Liu, Yong Li, Xu Wang, Xilei Xie, Xiaoyun Jiao, Bo Tang
Summary: A light-activatable photosensitizer based on a diarylethene derivative was developed for photodynamic therapy, showing sufficient therapeutic effects on HeLa cells. The opened form of DAE-TPE NPs was converted to the closed form upon UV exposure, activating photosensitization.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Loveleen Kaur Gulati, Gurleen Kaur Gulati, Satish Kumar
Summary: This article discusses the use of photochromism in photodynamic therapy, highlighting the potential of photochromic substances in three different roles to enhance efficacy: as photosensitizers, switches to conventional photosensitizers, and reserves of singlet oxygen.
Review
Chemistry, Multidisciplinary
Joern Bargstedt, Martin Reinschmidt, Leon Tydecks, Theresa Kolmar, Christoph M. Hendrich, Andres Jaeschke
Summary: Photochromic nucleosides have emerged as a promising approach for manipulating and studying complex processes in living organisms. This review highlights recent advancements in this field, including design principles, synthetic strategies, analytical challenges, and applications. The incorporation of photoswitchable moieties into biological macromolecules allows for light-responsive behavior, offering advantages in cellular and tissue applications due to its non-invasive nature. This field holds great potential for precise control of gene expression and modulation of biomolecular structure and function.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Daniela Pinheiro, Marta Pineiro, J. Sergio Seixas de Melo
Summary: Halogenated tryptanthrin and aminotryptanthrin were synthesized from indigo or isatin precursors, with spectral and photophysical properties including the dominant role of the triplet state (T-1) and the enhancement by halogens at the fused-phenyl rings. Substitution with an amino group led to a dominance of the radiative decay channel. The emission of the triplet state of tryptanthrin derivatives was observed, with an enhancement of the singlet oxygen sensitization quantum yield, showing a contrast with indigo and its derivatives in terms of singlet oxygen sensitization efficiency.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Materials Science, Multidisciplinary
Y. Wang, N. D. Alkhaldi, N. K. Pandey, L. Chudal, L. Y. Wang, L. W. Lin, M. B. Zhang, Y. X. Yong, E. H. Amador, M. N. Huda, W. Chen
Summary: This study introduces a series of cuprous-cysteamine sensitizers with tunable fluorescence and the ability to generate reactive oxygen species, showing different stability levels. The synthesis technique, optical properties, and potential applications of these materials, including photodynamic therapy, are discussed, opening up new possibilities in various fields.
MATERIALS TODAY PHYSICS
(2021)
Article
Chemistry, Multidisciplinary
Iumzhana A. Bolotova, Alexander O. Ustyuzhanin, Ekaterina S. Sergeeva, Anna A. Faizdrakhmanova, Yu Hai, Andrey V. Stepanov, Igor A. Ushakov, Konstantin A. Lyssenko, Lei You, Andrey G. Lvov
Summary: This study introduces the first versatile class of diarylethenes, potassium 2,3-diarylmaleates (DAMs), which show excellent solubility in water. DAMs feature a full spectrum of photoactivity in water, undergoing both irreversible and reversible reactions, making them suitable for a wide range of applications in organic synthesis, materials chemistry, and photopharmacology that require aqueous media for photochemical reactions.
Article
Optics
Evgeni M. Glebov, Veronica V. Semionova, Sofia K. Lazareva, Artem B. Smolentsev, Roman G. Fedunov, Valerii Z. Shirinian, Andrey G. Lvov
Summary: The introduction of a push-pull system in the ethene bridge of diarylethene allows for the preparation of multifunctional fluorescent switches. This system responds to various stimuli such as UV, visible light, solvent polarity, and pH change. The luminescent and photochromic properties of cyclopentenone-based derivatives were studied in various solvents, revealing a strong dependence on intramolecular charge transfer excited states and solvent polarity.
JOURNAL OF LUMINESCENCE
(2022)
Article
Materials Science, Multidisciplinary
Giovanni F. Cotella, Aurelio Bonasera, Giuseppe Carnicella, Alessandro Minotto, Stefan Hecht, Franco Cacialli
Summary: The study explores optically switchable organic light-emitting diodes (OSOLEDs) based on commercially available light-emitting polymer F8BT doped with a diarylethene derivative. The photochromic activity of the dopant in the solid state and morphology of different blends are investigated. The devices demonstrate a maximum reversible optical threshold voltage shift of 4 V with best performing devices showing a maximum current density and luminance ON/OFF ratio of approximately 20 and 90, respectively.
ADVANCED OPTICAL MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Theresa Kolmar, Simon M. Buellmann, Christopher Sarter, Katharina Hoefer, Andres Jaeschke
Summary: The study synthesized 26 systematically varied nucleosidic and oligonucleotidic diarylethenes, analyzing their reaction quantum yields, photostationary states, stability, and reversibility. Two high-performance photoswitches were identified, demonstrating potential for optochemical control of biological processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Marie Barale, Muriel Escadeillas, Gregory Taupier, Yann Molard, Clement Orione, Elsa Caytan, Remi Metivier, Julien Boixel
Summary: In this study, the first intramolecular excimer photoswitching induced by molecular motion within a dithienylethene (DTE) molecule without destructive readout was reported. The DTE-based pyrene compound displayed intense pyrene excimer luminescence upon both one-and two-photon excitation. The stability of the DTE-based pyrene under TPE irradiation and high photocyclization quantum yield allowed for nondestructive readout fluorescence.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Theresa Kolmar, Antonia Becker, Ronja A. Pfretzschner, Alina Lelke, Andres Jaeschke
Summary: This article discusses the systematic variation of the core structure in nucleoside-based diarylethenes to achieve reversible modulation of fluorescence signals by light. The introduction of different aromatic bridging units affects the absorption peak and switch efficiency of the closed-ring form, while the substitution of different aryl units in the core improves stability and fluorescence properties, holding potential applications in fluorescence-switchable DNA.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Biochemistry & Molecular Biology
Werner Fudickar, Phillip Roder, Martin Listek, Katja Hanack, Torsten Linker
Summary: Research found that the three isomeric methylpyridinium alkynylanthracenes 1op are effective sensitizers for photodynamic therapy, capable of initiating DNA strand breaks and impacting cellular integrity. Isomer 1m, which can be easily synthesized, is a promising candidate for cancer therapy.
PHOTOCHEMISTRY AND PHOTOBIOLOGY
(2022)
Article
Engineering, Environmental
Ziyong Li, Si Chen, Yurou Huang, Hui Zhou, Shuren Yang, Haining Zhang, Mingxing Wang, Hui Guo, Jun Yin
Summary: Researchers have developed a novel photosensitizer system that allows for reversible control over singlet oxygen generation. This photosensitizer exhibits excellent aggregation-induced emission properties and photoswitching behavior, making it suitable for precise photodynamic therapy.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Applied
Jia-Xing Wang, Xin Li, Chen Li
Summary: In this study, a new NIR absorbing photochromic DAE system was developed, utilizing a closed isomer with a TAA radical as the source of NIR absorption. The closed isomer TDEc-ox demonstrated NIR absorption upon light stimulation, showing high stability and a non-destructive readout. This system offers a convenient way to accumulate NIR absorbing material through photoisomerization cycles.
Article
Chemistry, Multidisciplinary
Yasunobu Kotani, Haruka Yasuda, Kenji Higashiguchi, Kenji Matsuda
Summary: A newly synthesized amphiphilic rectangular-shaped photochromic diarylethene exhibited a re-entrant photoinduced morphological transformation in water, with temperature-dependent kinetic products observed in the supramolecular assembly process. The behavior was rationalized by the temperature-dependent potential energy surface of the assembly.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Correction
Chemistry, Multidisciplinary
Shuaidong Huo, Pengkun Zhao, Zhiyuan Shi, Miancheng Zou, Xintong Yang, Eliza Warszawik, Mark Loznik, Robert Goestl, Andreas Herrmann
Article
Chemistry, Multidisciplinary
Zhuojun Meng, Qing Liu, Yi Zhang, Jing Sun, Chenjing Yang, Hongyan Li, Mark Loznik, Robert Gostl, Dong Chen, Fan Wang, Noel A. Clark, Hongjie Zhang, Andreas Herrmann, Kai Liu
Summary: The study introduces a DNA organogel that gels through supramolecular interactions, showing exceptional mechanical properties and biocompatibility, with complete self-healing within 3 seconds. These liquid crystalline organogels exhibit impressive ultimate tensile strengths, stiffness, and toughness, making them potential candidates for a wide range of smart material and biomedical applications.
ADVANCED MATERIALS
(2022)
Review
Chemistry, Multidisciplinary
Robin Kueng, Robert Goestl, Bernd M. Schmidt
Summary: The design and manipulation of (multi)functional materials at the nanoscale is of great importance for future technological advancements. Incorporating force-responsive groups allows for exploration of complex behaviors and functions of structures. Among various force-activated motifs, the on-demand release or activation of compounds is sought-after, enabling small molecule function from macromolecular frameworks. Ultrasound-induced mechanochemistry provides a solution for molecular cargo release from polymer-based architectures.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Robin Kueng, Anne Germann, Marcel Kruesmann, Louisa P. Niggemann, Jan Meisner, Matthias Karg, Robert Goestl, Bernd M. Schmidt
Summary: We have developed metal-organic cage-crosslinked polymer hydrogels by using bipyridine-functionalized polyethylene glycol chains. These hydrogels can encapsulate guest molecules and can be disassembled by ultrasound to release the cargo. The performance of the hydrogels was characterized by various techniques, including NMR, rheology, and SAXS experiments. The study also reveals the mechanism of cage-opening and demonstrates the enhanced drug-loading capacity of the hydrogels compared to non-crosslinked assemblies.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Tim Aguirre, Ellen Teichmann, Florian Q. Roempp, Ruthey Vivier, Cole Bryant, Matthew A. Hulverson, Wesley C. Van Voorhis, Kayode K. Ojo, J. Stone Doggett, Dorothea Fiedler, Stefan Hecht
Summary: This study developed photoswitchable azopyrazoles as inhibitors to selectively target CDPK1 from Toxoplasma gondii. The inhibitory activity of CDPK1 is dependent on the size of the gatekeeper residue. The photoswitchable inhibitors also showed activity against T. gondii and Cryptosporidium parvum infections in a cell culture model.
ACS CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Yu Zhou, Silvia P. Centeno, Kuan Zhang, Lifei Zheng, Robert Goestl, Andreas Herrmann
Summary: This study reports the development of a series of ratiometric optical force probes (OFPs) based on fluorescent-protein-dye and protein-protein conjugates, and their incorporation into genetically engineered bio-glues. The OFPs efficiently modulate Forster resonance energy transfer upon force application, reporting on force-induced molecular alterations independent of concentration and fluorescence intensity. By fluorescence spectroscopy in solution and in the solid state, as well as fluorescence lifetime imaging microscopy, stress concentrations are visualized and adhesive and cohesive failure in the fracture zone is differentiated.
ADVANCED MATERIALS
(2023)
Review
Chemistry, Multidisciplinary
Chung-Yang (Dennis) Huang, Stefan Hecht
Summary: This review explores the significance of indigo as a historical dye and its recent potential as a functional motif due to its intriguing photochemical properties. The synthesis of indigo core and available methods for derivatizing indigo are described, serving as synthetic strategies for building desired molecular structures. The photochemical behavior of indigos, particularly E-Z photoisomerization and photoinduced electron transfer, is discussed, emphasizing the connections between molecular structures and photochemical properties as guiding principles for designing indigos as photoresponsive tools.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Engineering, Biomedical
Prachi Desai, Anshuman Dasgupta, Alexandros Marios Sofias, Quim Pena, Robert Goestl, Ioana Slabu, Ulrich Schwaneberg, Thomas Stiehl, Wolfgang Wagner, Stefan Jockenhoevel, Julia Stingl, Rafael Kramann, Christian Trautwein, Tim H. Bruemmendorf, Fabian Kiessling, Andreas Herrmann, Twan Lammers
Summary: Drug delivery systems (DDS) control drug availability and activity to achieve a balance between therapeutic efficacy and side effects. They overcome biological barriers encountered by drug molecules and are explored for modulating host-material interfaces. This article provides an overview of barriers and interfaces encountered by DDS in different administration routes and highlights material engineering advances for improved disease treatment.
ADVANCED HEALTHCARE MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Mingjun Xuan, Jilin Fan, Vu Ngoc Khiem, Miancheng Zou, Kai-Oliver Brenske, Ahmed Mourran, Rostislav Vinokur, Lifei Zheng, Mikhail Itskov, Robert Goestl, Andreas Herrmann
Summary: Polymer mechanochemistry is a promising technology to convert mechanical energy into chemical functionality by breaking bonds. In this study, a microbubble system was used to accelerate the mechanochemical activation of disulfides, and optimization conditions were identified.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Lucas Stuewe, Matthias Geiger, Franz Roellgen, Thorben Heinze, Marcus Reuter, Matthias Wessling, Stefan Hecht, John Linkhorst
Summary: This study advances the volumetric 3D printing technique xolography to a continuous process, enabling the continuous printing of objects with true shape and high resolution. By performing dual-color photopolymerization in a flowing resin within a specially designed flow cell, this technique offers the potential to scale up volumetric 3D printing and resolve the trade-off between high production rates and high resolution in light-based additive manufacturing.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Siyang He, Simon Schog, Ying Chen, Yuxin Ji, Sinan Panitz, Walter Richtering, Robert Goestl
Summary: The serial connection of multiple stimuli-responses in polymer architectures enables the gating of functional material processes on demand. In this study, a photoswitchable diarylethene is used as a crosslinker in poly(N-vinylcaprolactam) microgels to induce a shift in volume phase-transition temperature (VPTT). By switching the microgels from the swollen to the collapsed state using light, their response to mechanical force can be controlled. This photoinduced mechanical cloaking system operates on a polymer topology level and is universally applicable.
ADVANCED MATERIALS
(2023)
Article
Chemistry, Multidisciplinary
Filippo Giovanni Fabozzi, Nikolai Severin, Jurgen P. Rabe, Stefan Hecht
Summary: In this study, the on-surface polymerization of a vinylene-linked single-layer two-dimensional covalent organic framework using reversible Knoevenagel polycondensation under solvothermal conditions was described. The self-assembly of monomer building blocks at the solid-liquid interface led to the formation of extended covalent networks at room temperature without the need for additional catalysts or reagents. This approach provides a new pathway for the synthesis of extended conjugated 2D polymers under mild conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Emilia Izak-Nau, Louisa P. Niggemann, Robert Goestl
Summary: Research has shown that iron oxide nanoparticles larger than 15 nm react to alternating magnetic fields by undergoing Brownian relaxation, resulting in tumbling and shaking. This shaking motion is able to partially detach and cleave polymer coatings, leading to the release of cargo molecules. Unlike traditional hyperthermia applications, this heat-free release mechanism broadens the potential application space of magnetic nanoparticles.
Article
Biochemical Research Methods
Ben Gerhardt, Kristin Klaue, Lennart Eigen, Jutta Schwarz, Stefan Hecht, Michael Brecht
Summary: Here, we introduce a X-ray-visible neural tracer called DiI-CT, which combines the well-known lipophilic indocarbocyanine dye DiI with two iodine atoms. This tracer is visible under microfocus computed tomography (microCT) imaging and retains the excellent tracing properties of DiI. We demonstrate the potential of DiI-CT in studying the vibrissa follicle-sinus complex, a structure with limited visual access and where 3D tissue structure is important, by revealing detailed innervation patterns. In the brain, DiI-CT tracing holds promise for validating indirect connectivity measures such as diffusion tensor imaging. In conclusion, the bimodal dye DiI-CT opens up new opportunities in neuroanatomy.
CELL REPORTS METHODS
(2023)
Article
Chemistry, Multidisciplinary
Kim Kuntze, Jani Viljakka, Matti Virkki, Chung-Yang (Dennis) Huang, Stefan Hecht, Arri Priimagi
Summary: By simple synthetic derivatisation, indigo dye can be converted into a red-light E-Z photoswitch, which exhibits negative photochromism and tuneable thermal isomerisation kinetics. This makes indigo derivatives highly attractive for materials and living systems applications. However, the translation of indigo photoswitching dynamics from solution to solid state, which is crucial for most applications, is not well understood. In this study, the photoswitching performance of six structurally distinct indigo derivatives in five polymers of varying rigidity is investigated. Three key strategies are identified to enable efficient photoswitching under red light: choosing a soft polymer matrix, creating free volume around the indigo molecules, and applying low dye loading to inhibit aggregation. Implementation of these strategies leads to isomerisation performance nearly identical to that in solution, paving the way for designing new red-light photochromic materials based on indigos.
