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Photo-responsive chiral cyclic molecular switches based on stiff stilbene

Published on Feb 1, 2016in Dyes and Pigments4.02
· DOI :10.1016/j.dyepig.2015.10.033
Ning Zhu1
Estimated H-index: 1
(ECUST: East China University of Science and Technology),
Xin Li38
Estimated H-index: 38
(KTH: Royal Institute of Technology)
+ 1 AuthorsXiang Ma30
Estimated H-index: 30
(ECUST: East China University of Science and Technology)
Cite
Abstract
Abstract Two novel photo-responsive chiral cyclic molecular switches constituted of stiff stilbene and binaphthyl moieties connected through alkyl chains of different length were fabricated. The cyclization synthetic strategy employed herein made it convenient to obtain the pure Z isomers rather than Z/E isomer mixtures. The detailed photo-switching behaviors of target compounds were studied by the UV–Vis absorption and circular dichroism spectra in dichloromethane. The twist angles of the binaphthyl of the switches were able to be reversibly modulated by Z/E isomerization of stiff stilbene unit under alternative UV light stimuli and influenced by the length of alkyl chain to some extent.
  • References (58)
  • Citations (4)
Cite
References58
Newest
Published on Aug 7, 2015in Journal of Organic Chemistry4.75
Fang Hu10
Estimated H-index: 10
,
Meijiao Cao9
Estimated H-index: 9
+ 2 AuthorsJun Yin27
Estimated H-index: 27
A cyanine-based dithienylethene is developed. Its photoisomerization shows that (1) the irradiation of visible light can induce cyclization while the cycloreversion takes place upon irradiation with UV light and (2) the addition of CN– can lead to cyclization and cycloreversion upon irradiation of UV light and visible light, respectively.
Published on Aug 1, 2015in Nature Chemistry23.19
Pintu K. Kundu8
Estimated H-index: 8
(Weizmann Institute of Science),
Dipak Samanta14
Estimated H-index: 14
(Weizmann Institute of Science)
+ 6 AuthorsRafal Klajn30
Estimated H-index: 30
(Weizmann Institute of Science)
Controlling the self-assembly of nanoparticles using light has been demonstrated in many systems where the particle surfaces are functionalized with photoswitchable ligands. Now, it has been shown that the light-controlled self-assembly of non-photoresponsive nanoparticles can be achieved in a quantitative and reversible fashion by placing them in a photoresponsive medium.
Published on Apr 8, 2015in Journal of the American Chemical Society14.70
Thomas Heinrich5
Estimated H-index: 5
,
Christoph H.-H. Traulsen9
Estimated H-index: 9
+ 7 AuthorsChristoph A. Schalley47
Estimated H-index: 47
Interfaces provide the structural basis for function as, for example, encountered in nature in the membrane-embedded photosystem or in technology in solar cells. Synthetic functional multilayers of molecules cooperating in a coupled manner can be fabricated on surfaces through layer-by-layer self-assembly. Ordered arrays of stimulus-responsive rotaxanes undergoing well-controlled axle shuttling are excellent candidates for coupled mechanical motion. Such stimulus-responsive surfaces may help int...
Published on Dec 22, 2014in Angewandte Chemie12.26
Zachary S. Kean15
Estimated H-index: 15
(Duke University),
Sergey Akbulatov7
Estimated H-index: 7
(University of Liverpool)
+ 3 AuthorsStephen L. Craig43
Estimated H-index: 43
(Duke University)
A catalyst that couples a photoswitch to the biaryl backbone of a chiral bis(phosphine) ligand, thus allowing photochemical manipulation of ligand geometry without perturbing the electronic structure is reported. The changes in catalyst activity and selectivity upon switching can be attributed to intramolecular mechanical forces, thus laying the foundation for a new class of catalysts whose selectivity can be varied smoothly and in situ over a useful range by controlling molecular stress experie...
Published on Dec 15, 2014in Angewandte Chemie12.26
Hui Chen20
Estimated H-index: 20
(ECUST: East China University of Science and Technology),
Xiang Ma30
Estimated H-index: 30
(ECUST: East China University of Science and Technology)
+ 1 AuthorsHe Tian92
Estimated H-index: 92
(ECUST: East China University of Science and Technology)
Development of self-healing and photostimulated luminescent supramolecular polymeric materials is important for artificial soft materials. A supramolecular polymeric hydrogel is reported based on the host–guest recognition between a β-cyclodextrin (β-CD) host polymer (poly-β-CD) and an α-bromonaphthalene (α-BrNp) polymer (poly-BrNp) without any additional gelator, which can self-heal within only about one minute under ambient atmosphere without any additive. This supramolecular polymer system ca...
Xuzhou Yan37
Estimated H-index: 37
(ZJU: Zhejiang University),
Jiang Fei Xu1
Estimated H-index: 1
(CAS: Chinese Academy of Sciences)
+ 4 AuthorsPeter J. Stang75
Estimated H-index: 75
(UofU: University of Utah)
Coordination-driven self-assembly is a synthetic method used to generate complex structures based on the simple formation of metal–ligand bonds between molecular building blocks. These building blocks can be functionalized in a variety of ways, endowing the process with a wide range of modularity and tunability. Here, a building block is used that changes its structure when it absorbs light. Because the geometry of each building block is a critical determinant of overall structure, when the prec...
Published on May 14, 2014in Chemical Reviews54.30
Xin Zhang3
Estimated H-index: 3
,
Jun Yin27
Estimated H-index: 27
,
Juyoung Yoon89
Estimated H-index: 89
Published on Apr 1, 2014in Dyes and Pigments4.02
Jingjing Cao4
Estimated H-index: 4
(ECUST: East China University of Science and Technology),
Shuaifan Wu6
Estimated H-index: 6
(ECUST: East China University of Science and Technology)
+ 3 AuthorsXiang Ma30
Estimated H-index: 30
(ECUST: East China University of Science and Technology)
Abstract The spiropyran monolayer covalently protected gold nanorod ( GNR ) hybrid was prepared and well characterized for the first time, which was stable, soluble and photo-responsive under certain light irradiation in organic solvent. The photochromism of the densely packed spiropyran monolayer on the surface of GNRs was found having effect on the surface plasmonic resonance (SPR) absorption of gold nanorods, namely inducing the intensity change of the two plasma absorption peaks at 786 and 5...
Published on Mar 26, 2014in Journal of the American Chemical Society14.70
Carson J. Bruns18
Estimated H-index: 18
(NU: Northwestern University),
Marco Frasconi28
Estimated H-index: 28
(NU: Northwestern University)
+ 5 AuthorsJ. Fraser Stoddart125
Estimated H-index: 125
We report the one-pot synthesis and electrochemical switching mechanism of a family of electrochemically bistable ‘daisy chain’ rotaxane switches based on a derivative of the so-called ‘blue box’ (BB4+) tetracationic cyclophane cyclobis(paraquat-p-phenylene). These mechanically interlocked molecules are prepared by stoppering kinetically the solution-state assemblies of a self-complementary monomer comprising a BB4+ ring appended with viologen (V2+) and 1,5-dioxynaphthalene (DNP) recognition uni...
Published on Feb 26, 2014in Journal of the American Chemical Society14.70
Kuang-Yen Chen6
Estimated H-index: 6
,
Oleksii Ivashenko12
Estimated H-index: 12
+ 6 AuthorsBen L. Feringa100
Estimated H-index: 100
Monolayers of fluorinated light-driven molecular motors were synthesized and immobilized on gold films in an altitudinal orientation via tripodal stators. In this design the functionalized molecular motors are not interfering and preserve their rotary function on gold. The wettability of the self-assembled monolayers can be modulated by UV irradiation.
Cited By4
Newest
Published on Jan 1, 2019in Physical Chemistry Chemical Physics3.57
Patrick R. Huddleston6
Estimated H-index: 6
(NTU: Nottingham Trent University),
Victor Volkov8
Estimated H-index: 8
(NTU: Nottingham Trent University),
Carole C. Perry44
Estimated H-index: 44
(NTU: Nottingham Trent University)
Diversity of photo-switching structural elements open up new opportunities in the engineering of light driven reshaping of matter, in catalysis on-click including photodynamic cancer therapy, in light sensitive transport control and in data storage. Assisted with quantum calculations we explore the photo-physical properties of novel 3,3-azothiophene molecular systems, the synthesis of which we reported recently. In the considered azothiophenes, upon exposure to radiation at 365 nm and at 530 nm...
Published on Jan 2, 2018in International Reviews in Physical Chemistry10.17
Gloria Bazargan1
Estimated H-index: 1
(Drexel University),
Karl Sohlberg22
Estimated H-index: 22
(Drexel University)
AbstractThe development of switchable mechanically interlocked molecular architectures (MIMAs) is an active area of experimental and theoretical research because the environmental-responsiveness of these systems makes them desirable candidates for incorporation into molecular machines. Presented here is a review of the recent literature that reports theoretical and computational studies of these topologically complex systems. Modelling strategies that have been applied to switchable MIMAs are an...
Published on Jan 1, 2018in Chemical Communications6.16
Yuan Wang5
Estimated H-index: 5
(CAS: Chinese Academy of Sciences),
Yancong Tian10
Estimated H-index: 10
(University of Liverpool)
+ 5 AuthorsRoman Boulatov23
Estimated H-index: 23
(University of Liverpool)
We report a new molecular design for optically triggered nm-scale translation of a submolecular component relative to another. We used a rotaxane-like molecule terminated at one end with stiff stilbene that served both as a chromophore to trigger the translation of the pillar[5]arene “wheel” and as a stopper to prevent its dethreading.
Published on Jan 1, 2018in Textile Research Journal1.61
Yong-Chan Chung20
Estimated H-index: 20
(University of Suwon),
Jin Cheol Bae1
Estimated H-index: 1
(Inje University),
Byoung Chul Chun21
Estimated H-index: 21
(Inje University)
Vinyl benzoate (VB series) and trans-stilbene (SB series) were added onto polyurethane (PU) via graft polymerization, and the spectroscopic, thermal, tensile, shape memory, and low-temperature flexibility properties of the resulting polymers were compared with those of unmodified PU. The melting temperature (Tm) and glass transition temperature (Tg) of the soft segments are not significantly different for the VB and SB series compared with unmodified PU. The tensile strengths of the VB and SB se...
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