Photomechanical Organic Crystals As Smart Materials for Advanced
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DOI:10.1002/chem.201805382 Minireview & Photochemistry |Reviews Showcase| Photomechanical Organic Crystals as Smart Materials for Advanced Applications Qi Yu,[a] Briana Aguila,[d] Jia Gao,[a] Peixin Xu,[a] Qizhe Chen,[a] Jie Yan,[a] DongXing,[a] YaoChen,[b] Peng Cheng,[a, c] Zhenjie Zhang,*[a, b, c] and Shengqian Ma*[d] Chem. Eur.J.2019, 25,5611–5622 5611 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim Minireview Abstract: Photomechanical molecular crystals are receiving crystalsduring irradiationare triggered by solid-state photo- much attentiondue to their efficient conversion of light into chemicalreactions and accompanied by phase transforma- mechanical work and advantages including faster response tion. This Minireview summarizesrecent developments in time;higher Young’s modulus;and orderedstructure, as growingresearch into photoresponsive molecular crystals. measured by single-crystal X-ray diffraction. Recently,various The basic mechanisms of different kinds of photomechanical photomechanical crystals with different motions (contrac- materialsare described in detail;recent advances in photo- tion, expansion,bending, fragmentation, hopping, curling, mechanical crystalsfor promising applications as smart ma- and twisting) are appearing at the forefront of smart materi- terials are also highlighted. als research. The photomechanical motionsofthese single 1. Introduction Various types of photomechanical motionshave been ob- served in photomechanical crystals, including jumping, ex- The conversion of externalenergy into macro-, micro-, or panding, bending, twisting, crawling, rolling,and even walking, nanoscopicmechanical motion by stimuli-responsivematerials upon irradiation with UV or visible light.The mechanical is of great interest from both fundamental and technological motion of crystalsisusually directly driven by the transforma- standpoints. Stimuli-responsive materials can presentdramatic tion of their molecular structure and molecular packing upon mechanical motionsunder the stimuli such as light irradia- exposure to stimuli.Dramatic crystal shape changes always tion,[1] heating,[2] externalforce,[3] solvent,[4] electrical fields,[5] originate from strain accumulation in the crystal interior and so on.[6] Amongthese stimuli,light is currently attracting caused by crystal structural transformations. Therefore, differ- increasing interestdue to its superior advantages, including ent light-sensitivechromophores associate with different pho- noncontact control, easy to obtain, cost-effectiveness, and vari- toresponsive mechanisms, including trans–cis isomerization of ous manipulatingmethods.[7] Various photomechanical materi- azobenzene, photocyclization of diarylethenes, [2+2] cycload- als, such as polymers,[8] elastomers,[9] liquid-crystalline materi- dition of olefins, [4+4] photodimerization of anthracene, and als,[10,11] andmolecular crystals,[12] have been reported, to date. other cis–trans isomerismtransformations. Commonly,photo- In particular, photomechanical crystals have attracted increas- mechanical molecular crystals can be classified into two types, ing attention because they not only have great potential for according to the recoveryconditions from photogenerated applicationsinlight harvesting, mechanical actuators,molecu- products to original phases, namely,Ttype (thermally revers- lar machines, optical sensors, and smart switches,[13] but also ible) and Ptype (thermally irreversible, but photochemically re- provide the opportunity to understand their performance versible).[15] Most photomechanical molecular crystals are of T throughXRD methods by solving ordered molecular struc- type, which requireheating to recover their photomechanical tures.[14] Compared with polymers, elastomers, and liquid-crys- ability,such as azobenzene, olefins, and anthracene. Only a talline materials, molecular crystals possess many advantages, few familiesofmolecular crystals can undergo photochemical- such as faster response times,[12] shorter recovery times, a ly reversible reactions, such as diarylethenes. higher Young’smodulus,[15] and awell-definedcrystal struc- To date, photomechanical behavior has been observed in ture.[16,17] In addition, light and mechanical energy transfer rap- molecular crystalsoforganic compounds, coordination com- idly occurs in orderedmolecular single crystalswith less plexes, and organometallic compounds. It should be noted energy dissipation. that most studies relatedtophotomechanical crystalsfocus on organic crystalsdue to their modular design natureand con- [a] Q. Yu,J.Gao, P. Xu, Q. Chen, J. Yan, D. Xing, Prof. P. Cheng, Prof. Z. Zhang venient synthesis. Herein, recent progress and development in College of Chemistry, Nankai University,Tianjin, 300071 (P.R. China) photomechanical organic crystals are summarized,and remarks E-mail:[email protected] on existing challenges and possible future directions in this [b] Prof. Y. Chen,Prof. Z. Zhang State Key Laboratory of Medicinal Chemical biology field are given. Nankai University,Tianjin,300071 (P.R. China) [c] Prof. P. Cheng, Prof. Z. Zhang Key Laboratory of Advanced EnergyMaterialsChemistry 2. Classification of Photomechanical Organic Ministry of Education, Nankai University,Tianjin, 30007 (P.R. China) Crystals Based on Photoreactions [d] B. Aguila, Prof. S. Ma 2.1 Photomechanical organic crystals inducedbytrans–cis Department of Chemistry,University of South Florida 4202 E. Fowler Avenue, Tampa, FL 33620 (USA) isomerization E-mail:[email protected] 2.1.1 The trans–cis isomerization of azobenzene Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: Azobenzene, adiazene (HN=NH) derivativeinwhich both hy- https://doi.org/10.1002/chem.201805382.Table S1 summarizes the molecu- drogen atoms are replaced by phenylgroups, is aprominent lar structure, irradiationconditions,and photomechanical behavior of the reported photoresponsive crystals. family of photomechanical molecules based on trans–cis iso- [18] Selected by the EditorialOffice for our Showcaseofoutstanding Review- merization. The trans–cis isomerization phase transition is type articles (www.chemeurj.org/showcase). usually driven by UV-lightirradiation, which causes large-scale Chem. Eur.J.2019, 25,5611–5622 www.chemeurj.org 5612 2019 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim Minireview deformation of the crystal shape and size. The reverse reaction it possible for applications in remote-controlled microsized of cis to trans isomerization occurs spontaneously at room valves on solid substrates. temperature in the dark due to the thermodynamic stability of The photoinducedbending behavior of azobenzene derivate the trans isomer relative to that of the cis isomer.Geometry crystalshas been widely studied. Under continuous UV excita- changes to azobenzene result in crystal motion,owing to tion, crystals bend continuously with arange of curvatures; strain accumulated in the crystals. Azobenzene and its deriva- this provides abasis to study effects of deformation. Upon kin- tives exhibit remarkable photostability and faster responses ematic analysis, the authors disentangled the relationship be- under light irradiation (Figure 1). Photoinducedbending of the tween intrinsic factors(the size and initial shape of the crystal) azobenzene crystal under UV-light irradiation was first reported and externalfactors(excitation power, direction, andtime) in in 2009.[19] The development of azobenzene photomechanical detail.[21] The trans–cis isomerization of azobenzene crystals crystalshas boomed in the past few years. Through modulat- was usually stimulatedbyUVirradiation, which greatly limited ing the substituent sites of azobenzene and interactions be- their practical applicationsdue to the inconvenience and po- tween molecules, variousmechanical motionsare exhibited. tential dangers of UV light. Thus,the preparation of azoben- zene crystals photoresponsive to visible light is of great signifi- cance. Barrett et al. reportedaseries of azobenzene com- pounds that responded to visible-light irradiation through modifying astrong electron-withdrawing “pull” group and a strong “push” donor in molecules of azobenzene.[22] This class Figure 1. Isomerization of azobenzene. Qi Yu received her BSc and MS degrees in 2013 and 2016 from Harbin University of Sci- ence and Technology (advisor: Professor Xiao- Norikaneand co-workersreported an azobenzene derivative, jun Sun). She was then recommended as a the 3,3-dimethylazobenzene (DMAB) crystal, whichexhibited PhD candidate toNankai University under the directional and continuous motion on aglass surfaceduring si- supervision of Prof. Peng Cheng and Prof. Zhenjie Zhang. Her research is focused on l multaneousirradiation at two different wavelengths ( = 365 photoresponsive crystalline materials and [20] and 465 nm;Figure 2). Moreover,crystals can climb on verti- solid-state chemistry. cal surfaces at room temperature. This trans–cis conversion in- duced liquefaction of the crystals;inother words, caused the crystalline phasetotransform into aliquid. This finding makes Dr.Zhenjie Zhang received his BSc and MS degrees from Nankai University(advisor:Pro- fessorPeng Cheng). In 2014 he obtained his PhD degree from the University of South Flori- da (advisor: Professor Michael J. Zaworotko). From 2014–2016, he was apostdoc at UC San Diego (Advisor:Seth Cohen). From 2016, he started his independentcareer atNankai University as afull professorofInorganic Chemistry. He is currently focusingonre- searchinseparation