Understanding X-ray-induced isomerisation in photoswitchable surfactant assemblies

• Beatrice E. Jones,
• Camille Blayo,
• Jake L. Greenfield,
• Matthew J. Fuchter,
• Nathan Cowieson and
• Rachel C. Evans

Beilstein J. Org. Chem. 2024, 20, 2005–2015, doi:10.3762/bjoc.20.176

• of smart materials whose properties can be controlled using external stimuli is of significant interest for diverse applications spanning soft robotics [1], energy storage [2] and drug delivery [3]. Light is an ideal stimulus as it is non-invasive and can be administered selectively with high

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

• Ka-Lung Hung,
• Leong-Hung Cheung,
• Yikun Ren,
• Ming-Hin Chau,
• Yan-Yi Lam,
• Takashi Kajitani and
• Franco King-Chi Leung

Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142

• functionalized with photoresponsive and photoabsorbing functional motifs, serving as the counterpart of natural photosystems. This allowed to construct smart materials that harvest light energy, e.g., solar cells, photosensitizers, and photochromic materials [1][2][3][4]. Supramolecular assemblies are commonly

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• application potential in biological systems and interactive "smart" materials that can adjust to environmental variations and respond to external light stimuli in a highly controllable manner. The prospective use of the indigoid photoswitches in photopharmacology [81][82][83][84][85][86] is especially

The effect of dark states on the intersystem crossing and thermally activated delayed fluorescence of naphthalimide-phenothiazine dyads

• Liyuan Cao,
• Xi Liu,
• Xue Zhang,
• Jianzhang Zhao,
• Fabiao Yu and
• Yan Wan

Beilstein J. Org. Chem. 2023, 19, 1028–1046, doi:10.3762/bjoc.19.79

• Liyuan Cao Xi Liu Xue Zhang Jianzhang Zhao Fabiao Yu Yan Wan State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, 2 Ling Gong Road, Dalian, 116024, P. R. China College of Chemistry, Beijing Normal

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• Adrian Saura-Sanmartin Departamento de Química Orgánica, Facultad de Química, Universidad de Murcia, 30100 Murcia, Spain 10.3762/bjoc.19.64 Abstract Light-responsive rotaxane-based solid-state materials are ideal scaffolds in order to develop smart materials due to the properties provided by the

• -responsive materials; mechanical bond; mechanically interlocked materials; rotaxanes; Introduction Light turns out to be a suitable and tailorable stimulus in order to develop materials showing improved functionalities, such as those of smart materials [1][2][3][4][5]. The characteristics of light which

• materials and molecular machinery operating through light stimuli. Thus, the construction of smart materials by the rotaxane approach leads to envision a promising future in the area of photoresponsive materials incorporating molecular machines. a) Chemical structure of pseudorotaxanes 1; and (b) single

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

• Kaiyue Ye,
• Liyuan Cao,
• Davita M. E. van Raamsdonk,
• Zhijia Wang,
• Jianzhang Zhao,
• Daniel Escudero and
• Denis Jacquemin

Beilstein J. Org. Chem. 2022, 18, 1435–1453, doi:10.3762/bjoc.18.149

• Kaiyue Ye Liyuan Cao Davita M. E. van Raamsdonk Zhijia Wang Jianzhang Zhao Daniel Escudero Denis Jacquemin State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China Department of

Trichloroacetic acid fueled practical amine purifications

• Aleena Thomas,
• Baptiste Gasch,
• Enzo Olivieri and
• Adrien Quintard

Beilstein J. Org. Chem. 2022, 18, 225–231, doi:10.3762/bjoc.18.26

• from rotaxanes, cucurbit[8]uril, to supramolecular smart materials [11][12][13][14][15][16]. TCA is also known for its application in the precipitation of proteins through what is believed to be an unfolding of the proteins structures [17][18]. In this context, we hypothesized that TCA could be used to

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• changes of environmental conditions because of their characteristic physical and chemical properties. For this reason, they are also referred to as "smart materials". Due to their very flexibly designable organic structure, the physicochemical properties of polymers can be adjusted precisely, making them

• ., bacteria, biomolecules [15], enzymes [16]) or physical stimuli (e.g., light [17][18][19], temperature [12][18], mechanical forces, as well as electric [20][21] and magnetic fields [22][23][24]) [1][25][26]. As a result of these environmental triggers, smart materials exhibit a defined reversible change in

Tuning the solid-state emission of liquid crystalline nitro-cyanostilbene by halogen bonding

• Subrata Nath,
• Alexander Kappelt,
• Matthias Spengler,
• Bibhisan Roy,
• Jens Voskuhl and
• Michael Giese

Beilstein J. Org. Chem. 2021, 17, 124–131, doi:10.3762/bjoc.17.13

• tuning of the fluorescence behaviour and mesomorphic properties of the assemblies. Keywords: fluorescence; halogen bonding; liquid crystal; Introduction Supramolecular chemistry has proven to be an efficient approach for the development of novel smart materials, since it relies on non-covalent

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

• Andreas H. Heindl and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

• allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes – ‘starazos’ – which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on

• of novel, multi-state photoresponsive systems for smart materials. Experimental 3,5-Dibromo-2′,4′,6′-trimethoxyazobenzene (15) [24]: 3,5-Dibromoaniline (9.99 g, 39.8 mmol, 1.00 equiv) was suspended in water (20 mL) and aq HBF4 (50%, 15 mL, 119 mmol, 3.0 equiv) was added. The suspension was cooled to

Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB₂-type host–guest-conjugated amphiphilic molecules for controlled drug delivery

• Yang Bai,
• Cai-ping Liu,
• Di Chen,
• Long-hai Zhuo,
• Huai-tian Bu and
• Wei Tian

Beilstein J. Org. Chem. 2019, 15, 1925–1932, doi:10.3762/bjoc.15.188

• based on noncovalent interactions with dynamic nature and reversible property have attracted increasing attention in the fields of biomedicine [1][2][3][4][5][6][7], smart materials [8][9][10], etc. As one common noncovalent interaction [11], host–guest interaction has been used to effectively create

Novel macrocycles – and old ones doing new tricks

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178

• diversified. They are not only tools for studying molecular recognition and molecular machines, but are also key components for sensing, supramolecular catalysis, (chiral) separation, drug delivery, or smart materials. Many new macrocycles have recently been reported, with pillararenes being one of the most

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

• Widukind Moormann,
• Daniel Langbehn and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 727–732, doi:10.3762/bjoc.15.68

• molecular switches in photo and mechanoresponsive macromolecules and other smart materials. Keywords: bridged azobenzene; diazocine; mechanophor; oxidative C–C coupling; photochrome; reductive azo cyclization; Introduction The field of photoresponsive materials is of growing interest [1][2][3]. Several

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• ) and the low content required. All these works on PC pave the way for highly reactive photosensitive systems that can be used for high tech applications: functional coatings, smart materials, new 3D printing resins, preparation of composites. Other development of PC can be expected in near future

A switchable [2]rotaxane with two active alkenyl groups

• Xiu-Li Zheng,
• Rong-Rong Tao,
• Rui-Rui Gu,
• Wen-Zhi Wang and
• Da-Hui Qu

Beilstein J. Org. Chem. 2018, 14, 2074–2081, doi:10.3762/bjoc.14.181

• microscopic units with traditional materials to achieve morphological changes or other novel properties in smart materials is continuously receiving wide attention. Hence, in recent years, scientists have put more interests on the macroscopic changes caused by the stimuli-responsiveness of constituent units

• because of the fact that the induction of active and functional groups make the preparation of rotaxanes more difficult and complicated. Therefore, it is urgent to enrich both the family of stimuli-responsive units and the methods for constructing this kind of smart materials. In this paper, we report the

• construct stimuli-responsive polymers and smart materials. Experimental General and materials 1H NMR and 13C NMR spectra were measured on a Bruker AV-400 spectrometer. The electronic spray ionization (ESI) mass spectra were tested on a LCT Premier XE mass spectrometer. Chemicals were used as received from

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• efficiency indeed depends on the effective occurrence of both electrostatic and hydrophobic interactions between the guest and the polymer lattice. Thus, our CaNS nanosponges can be considered as a new class of purely synthetic smart absorbent materials. Keywords: calixarenes; nanosponges; smart materials

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• dissipative self-assembling structures, creating new forms of smart materials [31][32][33][34][35]. Yet, we are severely limited by too few examples of systems which are both extensive enough to exhibit dynamics, and at the same time, simple enough to be tunable [36]. In this perspective, we will attempt to

• chemical dissipative networks from organic structures. This has resulted in numerous exciting examples, ranging from functional out-of-equilibrium systems that can perform logic operations to dissipative self-assembling structures, creating new forms of smart materials (Figure 3a–d) [31][32][33][34][35][74

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• reversibility of the solution/hydrogel transition is observed in rheological experiments. In vitro tests show that the PEG-b-PAA/cisplatin hydrogel has a sustained cisplatin release over three days and that it has a high cytotoxity towards human bladder carcinoma EJ cells. 5 Responsive smart materials

• stimuli-responsive materials collectively called “smart materials”. These include “self-healing materials” which after being disrupted can recover their former state through host–guest interactions. Some examples of these materials are now discussed. 5.1 Photo-responsive materials Among the better known

• properties may be tailored to give smart-materials possessing stimuli responsive characteristics exemplified by photo-, pH-, thermo-, and redox-responsivity and self-healing. Inevitably, many more novel polymer network systems incorporating cyclodextrins will appear; some of which will find exciting

Superstructures with cyclodextrins: Chemistry and applications II

• Gerhard Wenz

Beilstein J. Org. Chem. 2015, 11, 271–272, doi:10.3762/bjoc.11.30

• smart materials and drug delivery. These contributions to Cyclodextrin Chemistry are collected in this Thematic Series of the Beilstein Journal of Organic Chemistry. Gerhard Wenz Saarbrücken, January 2015

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

• Alexander Burkhart and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

• water and vice versa, to a decrease of UCST in ethanol. According to that, these novel copolymers are of potential interest for the development of new types of smart materials. Experimental Materials and methods All reactants were commercially available and used without further purification. All

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

• Sourav Chakraborty,
• Snehasish Mondal,
• Rina Kumari,
• Sourav Bhowmick,
• Prolay Das and
• Neeladri Das

Beilstein J. Org. Chem. 2014, 10, 1290–1298, doi:10.3762/bjoc.10.130

• , polymers, supramolecules and other smart materials [2][3][4][5][6][7][8]. In order to explore more applications of triptycenes, there is a need to design newer derivatives of triptycene having specific functional groups. It is well established that aromatic azides are an important class of compounds having

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• interactions in living systems [3][4]. Since then, the field of self-assembly through molecular recognition has attracted much attention also in the design of smart materials. In this context, cyclodextrins (CD) are of interest as ring shaped host molecules, e.g., for the design of stimuli-responsive hydrogels

Cyclodextrin-induced host–guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

• Gero Maatz,
• Arkadius Maciollek and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935, doi:10.3762/bjoc.8.224

• techniques. Water-soluble polymers, which exhibit a lower critical solution temperature (LCST), e.g., many poly(N-alkylacrylamides), have found numerous practical applications in waterborne smart materials such as bioactive surfaces, selective bioseparation, or hyperthermia-induced drug delivery [14

Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives

• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1890–1895, doi:10.3762/bjoc.8.218

• the future help to design improved hosts based on β-CD for specific applications such as drug delivery [49], removal of pollutants [50][51][52][53], catalysis [54] or smart materials [55]. Experimental 4-tert-Butylbenzoic acid and adamantane-1-carboxylic acid and β-CD derivative 3 were purchased from