Second Generation Zwitterionic Aza‐Diarylethene: Photoreversible CN Bond Formation, Three‐State Photoswitching, Thermal Energy Release, and Facile Photoinitiation of Polymerization DOI Creative Commons
Henry Dube,

Maximilian Sacherer

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Abstract Diarylethenes are a well‐studied and optimized class of photoswitches with wide range applications, including data storage, smart materials, or photocontrolled catalysis biological processes. Most recently, aza‐diarylethenes have been developed in which carbon‐carbon bond connections replaced by carbon‐nitrogen connections. This structural elaboration opens up an entire new structure property space expanding the versatility applicability diarylethenes. In this work, we present second generation zwitterionic aza‐diarylethenes, finally allows for fully reversible photoswitching precise control over all three switching states. High‐yielding between neutral open form Z isomer is achieved two different wavelengths light. The third E isomeric state can be reached to 87 % upon irradiation wavelength. Its high energy content >10 kcal/mol released thermally deliberate solvent change as trigger mechanism, rendering into interesting candidates molecular solar thermal storage (MOST) applications. also serves locking state, allowing toggle light‐responsiveness reversibly labile stable switching. Further, states leads highly efficient photopolymerization methyl acrylate (MA), directly harnessing unleashed chemical reactivity our aza‐diarylethene materials application.

Language: Английский

Deciphering the Role of Rhodanine Flanked Non-Fullerene Acceptor Molecules for Efficient Organic Photovoltaics DOI Open Access
Zobia Irshad, Muzammil Hussain, Riaz Hussain

et al.

International Journal of Molecular Sciences, Journal Year: 2025, Volume and Issue: 26(7), P. 3314 - 3314

Published: April 2, 2025

In recent years, extensive research has been conducted with the aim of developing non-fullerene acceptors as they have a promising ability to drive development cost-effective and highly efficient organic solar cells (OSCs). By harnessing potential rhodanine-flanked (NFAs), we proposed eight new A-D-A type NFAs (SBA1-SBA8) through precise end-cap modifications on both sides bridging-core unit. We performed various advanced quantum chemical analyses unveil these designed materials' compared them synthetic reference molecule (R). The series presented lower binding excitation energy, along narrower energy gaps 2.11 eV enhanced absorption at 671.20 nm 719.88 in gaseous chloroform environments, respectively. Furthermore, optoelectronic photophysical characterizations related electrostatic potential, density states, reorganization electron hole mobilities, transition matrix analysis reveal that materials could be efficiently used acceptor for photovoltaics. Additionally, check impact charge transfer donor: (D: A) interface, studied PTB7-Th:SBA1 D:A demonstrated remarkable interface phenomenon. Therefore, engineered SBA1-SBA8 represent significant advancement sustainable effective options high-performance OSCs.

Language: Английский

Citations

1
Ion-selective response of visible light photoswitchable indole-hemithioindigo: toward chemical sensing of fluoride and hydroxide DOI
Weian Zhang, Yi Lü,

Yu Cheng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4202 - 4205

Published: Jan. 1, 2024

A visible light responsive photoswitch promising for the chemical sensing of fluoride and hydroxide anions.

Language: Английский

Citations

4
Getting a molecular grip on the half-lives of iminothioindoxyl photoswitches DOI Creative Commons

Melody E. Boëtius,

Mark W. H. Hoorens,

Martin Ošťadnický

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(35), P. 14379 - 14389

Published: Jan. 1, 2024

Visible-light-operated photoswitches are of growing interest in reversibly controlling molecular processes, enabling for example the precise spatiotemporal focusing drug activity and manipulating properties materials. Therefore, many research efforts have been spent on seeking control over (photo)physical photoswitches, particular absorption maxima half-life. For photopharmacological applications, should ideally be operated by visible light at least one direction, feature a metastable isomer with half-life 0.1-10 seconds. Here we present our towards engineering iminothioindoxyl (ITI) recently discovered class visible-light-responsive photochromes, whose applicability was hitherto limited half-lives low millisecond range. Through synthesis characterization library ITI variants substantially increased thermal stability, reaching up to 0.2 Based spectroscopic computational analyses, demonstrate how different substituent positions molecule can used tune its photophysical independently fit desired application. Additionally, unique reactivity derivative that featured perfluoro-aromatic ring had most long-lived state shown useful labeling nucleophilic functional groups. The thus paves way using photopharmacology chemical biology.

Language: Английский

Citations

4
Hemiphosphoindigos as a platform for chiroptical or water soluble photoswitching DOI Creative Commons

Fabien Kohl,

Thomas Vogl, Frank Hampel

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 19, 2025

Abstract Photoswitches are important molecular tools to precisely control the behavior of matter by using light irradiation. They have found application in virtually all applied chemical fields from biology material sciences. However, great challenges remain advanced property design including tailored chiroptical responses or water solubility. Here, hemiphosphoindigo (HPI) photoswitches presented as capable phosphorus-based and a distinct addition established indigoid chromophore family. Phosphinate is embedded core resulting optimized display high thermal stabilities, excellent fatigue resistance isomer enrichment. A series planar, twisted heterocyclic HPIs investigated probe strategies for advantageous photophysical properties. The phosphinate provides platform easily accessible, water-soluble photoswitches, especially interesting biological applications. Its chiral nature further allows light-induced modulation therefore open up structural space photoswitch generation light-responsive

Language: Английский

Citations

0
Path‐Independent All‐Visible Orthogonal Photoswitching for Applications in Multi‐Photochromic Polymers and Molecular Computing DOI Creative Commons

Laura Köttner,

Henry Dube

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(44)

Published: July 3, 2024

Abstract Synthetic molecular photoswitches have taken center stage as high‐precision tools to introduce light‐responsiveness at the smallest scales. Today they are found in all areas of applied chemistry, covering materials research, chemical biology, catalysis, or nanotechnology. For a next step applicability truly orthogonal photoswitching is highly desirable but date such independent addressability different remains challenging. Herein we present first example all‐visible, all‐light responsive, and path‐ photoswitching. By combining two recently developed indigoid ‐ peri‐anthracenethioindigo rhodanine‐based chromophore four‐state system established each state can be accessed high yields completely independently also with visible light irradiation only. The four states give rise colors, which transferred solid polymer matrix yield versatile multi‐state photochromic material. Further, combination fluorescent dye third component possible, demonstrating this all‐photonic logic behavior information processing.

Language: Английский

Citations

3
Algorithm in chemistry: molecular logic gate-based data protection DOI
Yu Dong, Shiyu Feng, Weiguo Huang

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review focuses on stimuli-responsive material (SRM)-based data protection, emphasizing the integration of intricate logic and algorithms in SRM-constructed hardware. It also discusses current challenges future directions field.

Language: Английский

Citations

0
Dicyanorhodanine-Pyrrole Conjugates for Visible Light-Driven Quantitative Photoswitching in Solution and the Solid State DOI
Parag Das,

Nathan J. Grinalds,

Ion Ghiviriga

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(17), P. 11932 - 11943

Published: April 17, 2024

Small molecule photoswitches capable of toggling between two distinct molecular states in response to light are versatile tools monitor biological processes, control photochemistry, and design smart materials. In this work, six novel dicyanorhodanine-based pyrrole-containing reported. The avails both the

Language: Английский

Citations

3
Spectroscopic and SERS investigations of (E)-3-[(3-methoxybenzylidene) amino]rhodanine – experimental, DFT and MD analyses in solvents DOI
Jamelah S. Al‐Otaibi, Y. Sheena Mary, Y. Sheena Mary

et al.

Journal of the Indian Chemical Society, Journal Year: 2024, Volume and Issue: 101(8), P. 101205 - 101205

Published: June 4, 2024

Language: Английский

Citations

2
Path-independent all-visible orthogonal photoswitching for applications in multi-photochromic polymers and molecular computing DOI Creative Commons

Laura Köttner,

Henry Dube

Published: May 17, 2024

Synthetic molecular photoswitches have taken center stage as high-precision tools to introduce light-responsiveness at the smallest scales. Today they are found in all areas of applied chemistry, covering materials research, chemical biology, catalysis, or nanotechnology. For a next step applicability truly orthogonal photoswitching is highly desirable but date such fully independent addressability different remains be extremely challenging. In this work we present first example all-visible, all-light responsive, path independent, and photoswitching. By combining two recently developed indigoid - peri-anthracenethioindigo rhodanine-based chromophore four-state system established each state can accessed very high yields completely independently also with visible light irradiation only. The four states give rise colors, which transferred solid polymer matrix yielding multi-state photochromic material versatility. Further, combination fluorescent dye third component possible elevating all-photonic logic behavior information processing system.

Language: Английский

Citations

1
Combined Photopolymerization and Localized Photochromism Generation by Aza-Diarylethene and Hemiindigo Synergy DOI Creative Commons

Maximilian Sacherer,

Henry Dube

Published: Aug. 1, 2024

Molecular photoswitches produce light-controlled changes at the nanometer scale and can therefore be used to alter states behavior of materials in a truly bottom-up fashion. Here we show an escalating photonic complexity material property control with light using recently developed aza-diarylethene combination hemiindigo (HI) photoswitches. First, as photoswitch polystyrene (PS) inscribe relief-type 3D structures reversibly into PS. Second, aza- diarylethene further photoinitiator for light-induced polymerization acrylates, demonstrating first time chemical reactivity its zwitterionic switching state. Third, HIs are implemented polymerized PMA, generating photochromic polymers. At fourth level, binary mixture allows synergize induced photopolymerization localized photochromism simultaneously entrapped functional HI. With such multi-level response, utility this particular applications advanced is demonstrated.

Language: Английский

Citations

1