Diarylethene Dyes

References

[1] Irie M. Discovery and development of photochromic diarylethenes. Pure Appl Chem. 2015;87:617–26.10.1515/pac-2015-0208Search in Google Scholar

[2] Towns A. Photochromic Dyes. to be submitted.Search in Google Scholar

[3] Towns A. Naphthopyran dyes. Phys Sci Rev. 2020;5:20190085.10.1515/psr-2019-0085Search in Google Scholar

[4] Takame S, Kobatake S, Kawai T, Irie M. Extraordinarily high thermal stability of the closed-ring isomer of 1,2-Bis(5-methyl-2-phenylthiazol-4-yl)perfluorocyclopentene. Chem Lett. 2003;32:892–3.10.1246/cl.2003.892Search in Google Scholar

[5] Animoto K, Kawato T. Photochromism of organic compounds in the crystal state. J Photochem Photobiol C Photochem Rev. 2005;6:207–26.10.1016/j.jphotochemrev.2005.12.002Search in Google Scholar

[6] Irie M. Photoswitchable Molecular Systems based on Diarylethenes. In: Feringa BL, editor(s). Molecular switches, 1st ed. Weinheim: Wiley-VCH. Chapter 2. 2001:37–62.10.1002/3527600329.ch2Search in Google Scholar

[7] Nakatani K, Piard J, Yu P, Métivier R. Chapter 1 Introduction: organic photochromic molecules. In: Tian H, Zhang J editors, Photochromic materials: preparation, properties and applications, 1–45. Weinheim: Wiley-VCH, 2016.Search in Google Scholar

[8] Irie M. Diarylethenes for memories and switches. Chem Rev. 2000;100:1685–716.10.1021/cr980069dSearch in Google Scholar PubMed

[9] Irie M, Fukaminato T, Matsuda K, Kobatake S. Photochromism of diarylethene molecules and crystals: memories, switches and actuators. Chem Rev. 2014;114:12174–277.10.1021/cr500249pSearch in Google Scholar PubMed

[10] Nakashima T, Kawai T. Chapter 10 Photochromic terarylenes. In: Irie M, Yokoyama Y, Seki T editors, New frontiers in photochromism, 183–204. Tokyo: Springer, 2013.10.1007/978-4-431-54291-9_10Search in Google Scholar

[11] Lvov AG, Khusniyarov MM, Shirinian VZ. Azole-based diarylethenes as the next step towards advanced photochromic materials. J Photochem Photobiol C Photochem Rev. 2018;36:1–23.10.1016/j.jphotochemrev.2018.04.002Search in Google Scholar

[12] Uchida K, Nakayama Y, Irie M. Thermally irreversible photochromic systems. reversible photocyclisation of 1,2-Bis(benzo[b]thiophen-3-yl)ethene derivatives. Bull Chem Soc Jpn. 1990;63:1311–15.10.1246/bcsj.63.1311Search in Google Scholar

[13] Kitagawa D, Sasaki K, Kobatake S. Correlation between steric substituent constants and thermal cycloreversion reactivity of diarylethene closed-ring isomers. Bull Chem Soc Jpn. 2011;84:141–7.10.1246/bcsj.20100274Search in Google Scholar

[14] Kitagawa D, Kobatake S. Strategy for molecular design of photochromic diarylethenes having thermal functionality. Chem Rec. 2016;16:2005–15.10.1002/tcr.201600060Search in Google Scholar

[15] Uchida K, Tsuchida E, Aoi Y, Nakamura S, Irie M. Substitution effect on the coloration quantum yield of a photochromic bisbenzothienylethene. Chem Lett. 1999;28:63–4.10.1246/cl.1999.63Search in Google Scholar

[16] For example, Tokyo Chemical Industry. Photochromic dyes. www.tcichemicals.com/eshop/en/gb/category_index/12989/ Accessed: 25 Feb 2020.Search in Google Scholar

[17] Lucas LN, de Jong JJ, van Esch JH, Kellogg RM, Feringa BL. Syntheses of dithienylcyclopentene optical molecular switches. Eur J Org Chem. 2003;155–66.10.1002/1099-0690(200301)2003:1<155::AID-EJOC155>3.0.CO;2-SSearch in Google Scholar

[18] Szalóki G, Pozzo J-L. Synthesis of symmetrical and non-symmetrical bisthienylcyclopentenes. Chem Eur J. 2013;19:11124–32.10.1002/chem.201301645Search in Google Scholar

[19] Chen S, Li W, Zhu W-H. Chapter 2 Novel ethene-bridged diarylethene photochromic systems: self-assembly, photoswitcher, and molecular logic gates. In: Yokoyama Y, Nakatani K editors, Photon-working switches, 37–62. Tokyo: Springer, 2017.10.1007/978-4-431-56544-4_2Search in Google Scholar

[20] Nakayama Y, Hayashi K, Irie M. Themally irreversible photochromic systems. reversible photocyclisation of non-symmetric diarylethene derivatives. Bull Chem Soc Jpn. 1991;64:789–95.10.1246/bcsj.64.789Search in Google Scholar

[21] Uchida K, Irie M. A photochromic dithienylethene that turns yellow by UV irradiation. Chem Lett. 1995;24:969–70.10.1246/cl.1995.969Search in Google Scholar

[22] Hanazawa M, Sumiya R, Horikawa Y, Irie M. Thermally irreversible photochromic systems. reversible photocyclization of 1,2-bis (2-methylbenzo[b]thiophen-3-yl)perfluorocycloalkene derivatives. J Chem Soc Chem Commun. 1992;206–7.10.1039/c39920000206Search in Google Scholar

[23] Irie M, Sakemura K, Okinaka M, Uchida K. Photochromism of dithienylethenes with electron-donating substituents. J Org Chem. 1995;60:8305–9.10.1021/jo00130a035Search in Google Scholar

[24] Gilat SL, Kawai SH, Lehn J-M. Light-triggered electrical and optical switching devices. J Chem Soc Chem Commun. 1993;1439–42.10.1039/c39930001439Search in Google Scholar

[25] Zhang Z, Wang W, Jin P, Xue J, Sun L, Huang J, et al. A building-block design for enhanced visible-light switching of diarylethenes. Nat Commun. 2019;10:4232.10.1038/s41467-019-12302-6Search in Google Scholar

[26] Jia S, Fong W-K, Graham B, Boyd BJ. Photoswitchable molecules in long-wavelength light-responsive drug delivery: from molecular design to applications. Chem Mater. 2018;30:2873–87.10.1021/acs.chemmater.8b00357Search in Google Scholar

[27] Fredrich S, Goestl R, Herder M, Grubert L, Hecht S. Switching diarylethenes reliably in both directions with visible light. Angew Chem Intl Ed Engl. 2016;55:1208–12.10.1002/anie.201509875Search in Google Scholar

[28] Irie M, Lifka T, Kobatake S, Kato N. Photochromism of 1,2-Bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in a Single-Crystalline Phase. J Am Chem Soc. 2000;122:4871–6.10.1021/ja993181hSearch in Google Scholar

[29] Takami S, Kawai T, Irie M. Photochromism of dithiazolylethenes having methoxy groups at the reaction centers. Eur J Org Chem. 2002;22:3796–800.10.1002/1099-0690(200211)2002:22<3796::AID-EJOC3796>3.0.CO;2-XSearch in Google Scholar

[30] Yamaguchi T, Irie M. Photochromic and fluorescent properties of bisfurylethene derivatives. J Mater Chem. 2006;16:4690–4.10.1039/b611294cSearch in Google Scholar

[31] Kuroki L, Takami S, Shibata K, Irie M. Photochromism of single crystals composed of dioxazolylethene and dithiazolylethene. Chem Commun. 2005;6005–7.10.1039/b512873kSearch in Google Scholar

[32] Uchida K, Ishikawa T, Takeshita M, Irie M. Thermally irreversible photochromic systems. reversible photocyclization of 1,2-Bis(thiazolyl) perfluorocydopentenes. Tetrahedron. 1998;54:6627–38.10.1016/S0040-4020(98)00330-5Search in Google Scholar

[33] Hohlneicher G, Mueller M, Demmer M, Lex J, Penn JH, Gan L-X, et al. 1,2-diphenylcycloalkenes: electronic and geometric structures in the gas phase, solution, and solid state. J Am Chem Soc. 1988;110:4483–94.10.1021/ja00222a001Search in Google Scholar

[34] Zhu W, Yang Y, Métivier R, Zhang Q, Guillot R, Xie Y, et al. Unprecedented stability of a photochromic bisthienylethene based on benzobisthiadiazole as an ethene bridge. Angew Chem Intl Ed. 2011;50:10986–90.10.1002/anie.201105136Search in Google Scholar

[35] Wu Y, Guo Z, Zhu W-H, Wan W, Zhang J, Li W, et al. Photoswitching between black and colourless spectra exhibits resettable spatiotemporal logic. Mater Horiz. 2016;3:124–9.10.1039/C5MH00223KSearch in Google Scholar

[36] Irie M, Lifka T, Uchida K, Kobatake S, Shindo Y. Fatigue resistant properties of photochromic dithienylethenes: by-product formation. Chem Commun. 1999;747–50.10.1039/a809410aSearch in Google Scholar

[37] Jean-Ruel H, Cooney RR, Gao M, Lu C, Kochman MA, Morrison CA, et al. Femtosecond dynamics of the ring closing process of diarylethene: a case study of electrocyclic reactions in photochromic single crystals. J Phys Chem A. 2011;115:13158–68.10.1021/jp205818hSearch in Google Scholar

[38] Kellogg RM, Groen B, Wynberg H. Photochemically induced cyclization of some furyl- and thienylethenes. J Org Chem. 1967;32:3093–100.10.1021/jo01285a035Search in Google Scholar

[39] Irie M. Chapter 5 Diarylethenes with heterocyclic aryl groups. In: Crano JC, Guglielmetti RJ editors, Organic photochromic and thermochromic compounds volume 1: main photochromic families, 207–22. New York: Plenum, 1999.Search in Google Scholar

[40] Matsuda K, Irie M. Diarylethene as a photoswitching unit. J Photochem Photobiol C Photochem Rev. 2004;5:169–82.10.1016/S1389-5567(04)00023-1Search in Google Scholar

[41] Warford CC, Lemieux V, Branda NR. Chapter 1. Multifunctional diarylethenes. In: Feringa BL, Browne WR, editors. Molecular switches. 2nd ed. Weinheim: Wiley-VCH, 2011:3–35.Search in Google Scholar

[42] Zhang J, Tian H. The endeavor of diarylethenes: new structures, high performance, and bright future. Adv Opt Mater. 2018;6:1701278.10.1002/adom.201701278Search in Google Scholar

[43] Yokoyama Y, Nakatani K, eds. Photon-working switches. Tokyo: Springer, 2017.10.1007/978-4-431-56544-4Search in Google Scholar

[44] Stellacci F, Bertarelli C, Toscano F, Gallazzi MC, Zerbi G. Diarylethene-based photochromic rewritable optical memories: on the possibility of reading in the mid-infrared. Chem Phys Lett. 1999;302:563–70.10.1016/S0009-2614(99)00129-3Search in Google Scholar

[45] Minkin VI. Bistable organic, organometallic, and coordination compounds for molecular electronics and spintronics. Russ Chem Bull Int Ed. 2008;57:687–717.10.1007/s11172-008-0111-ySearch in Google Scholar

[46] Bertarelli C, Bianco A, Castagna R, Pariani G. Photochromism into optics: opportunities to develop light-triggered optical elements. J Photochem Photobiol C Photochem Rev. 2011;12:106–25.10.1016/j.jphotochemrev.2011.05.003Search in Google Scholar

[47] Feringa BL, van Delden RA, Koumura N, Geertsema EM. Chiroptical molecular switches. Chem Rev. 2000;100:1789–816.10.1002/3527600329.ch5Search in Google Scholar

[48] Nakagawa T, Ubukata T, Yokoyama Y. Chirality and stereoselectivity in photochromic reactions. J Photochem Photobiol C Photochem Rev. 2018;34:152–91.10.1016/j.jphotochemrev.2017.12.004Search in Google Scholar

[49] Bisoyi HK, Li Q. Light-driven liquid crystalline materials: from photo-induced phase transitions and property modulations to application. Chem Rev. 2016;116:15089–166.10.1021/acs.chemrev.6b00415Search in Google Scholar PubMed

[50] Göstl R, Senf A, Hecht S. Remote-controlling chemical reactions by light: Towards chemistry with high spatio-temporal resolution. Chem Soc Rev. 2014;43:1982–96.10.1039/c3cs60383kSearch in Google Scholar PubMed

[51] Wang L, Li Q. Photochromism into nanosystems: towards lighting up the future nanoworld. Chem Soc Rev. 2018;47:1044–97.10.1039/C7CS00630FSearch in Google Scholar

[52] Hüll K, Morstein J, Trauner D. In vivo photopharmacology. Chem Rev. 2018;118:10710–47.10.1021/acs.chemrev.8b00037Search in Google Scholar PubMed

[53] Ihrig SP, Eisenreich F, Hecht S. Photoswitchable polymerization catalysis: state of the art, challenges, and perspectives. Chem Commun. 2019;55:4290–8.10.1039/C9CC01431DSearch in Google Scholar PubMed

[54] Mostafavi SH, Tong F, Dugger TW, Kisailus D, Bardeen CJ. Noncovalent photochromic polymer adhesion. Macromol. 2018;51:2388–94.10.1021/acs.macromol.8b00036Search in Google Scholar

[55] Pu S-Z, Sun Q, Fan C-B, Wang R-J, Liu G. Recent advances in diarylethene-based multi-responsive molecular switches. J Mater Chem C. 2016;4:3075–93.10.1039/C6TC00110FSearch in Google Scholar

[56] Nevskyi O, Sysoiev D, Dreier J, Stein SC, Oppermann A, Lemken F, et al. Fluorescent diarylethene photoswitches – A universal tool for super-resolution microscopy in nanostructured materials. Small. 2018;14:1703333.10.1002/smll.201703333Search in Google Scholar

[57] Tsivgoulis GM, Lehn J-M. Photonic molecular devices: reversibly photoswitchable fluorophores for nondestructive readout for optical memory. Angew Chem Int Ed. 1995;34:1119–22.10.1002/anie.199511191Search in Google Scholar

[58] Guo F, Guo Z. Inspired smart materials with external stimuli responsive wettability: a review. RSC Adv. 2016;6:36623–41.10.1039/C6RA04079ASearch in Google Scholar

[59] Dunne A, Francis W, Delaney C, Florea L, Diamond D. Stimuli-controlled fluid control and microvehicle movement in microfluidic channels, reference module in materials science and materials engineering. Elsevier, 2017. http://doi.org/10.1016/B978-0-12-803581-8.04043-1 Accessed: 25 Feb 2020.10.1016/B978-0-12-803581-8.04043-1Search in Google Scholar

[60] Towns A. Colorants: general survey. Phys Sci Rev. 2019;4. DOI: 10.1515/psr-2019-0008.Search in Google Scholar

[61] Norsten TB, Branda NR. Axially coordinated porphyrinic photochromes for non-destructive information processing. Adv Mater. 2001;13:347–9.10.1002/1521-4095(200103)13:5<347::AID-ADMA347>3.0.CO;2-9Search in Google Scholar

[62] Higashiguchi K, Matsuda K, Tanifuji N, Irie M. Full-color photochromism of a fused dithienylethene trimer. J Am Chem Soc. 2005;127:8922–3.10.1021/ja051467iSearch in Google Scholar

[63] Tsujioka T, Irie M. Electrical functions of photochromic molecules. J Photochem Photobio C Photochem Rev. 2010;11:1–14.10.1016/j.jphotochemrev.2010.02.001Search in Google Scholar

[64] Gilat SL, Kawai SH, Lehn J-M. Light-triggered molecular devices: photochemical switching of optical and electrochemical properties in molecular wire type diarylethene species. Chem Eur J. 1995;1:275–84.10.1002/chem.19950010504Search in Google Scholar

[65] Kawai T, Kunitake T, Irie M. Novel photochromic conducting polymer having diarylethene derivative in the main chain. Chem Lett. 1999;28:905–6.10.1246/cl.1999.905Search in Google Scholar

[66] Gentili PL, Giubila MS, Germani R, Heron BM. Photochromic and luminescent compounds as artificial neuron models. Dyes Pigm. 2018;156:149–59.10.1016/j.dyepig.2018.04.006Search in Google Scholar

[67] Galbraith CA, Galbraith JA. Super-resolution microscopy at a glance. J Cell Sci. 2011;124:1607–11.10.1242/jcs.080085Search in Google Scholar PubMed PubMed Central

[68] Hell SW. Nanoscopy with Focused Light (Nobel Lecture). Angew Chem Int Ed. 2015;54:8054–66.10.1002/anie.201504181Search in Google Scholar PubMed

[69] Pujals S, Feiner-Gracia N, Albertazzi L. Unveiling complex structure and dynamics in supramolecular biomaterials using super-resolution microscopy. In: Azevedo HS, da Silva RM, editor(s). Self-assembling biomaterials: molecular design, characterization and application in biology and medicine. Kidlington: Woodhead. Chapter 12 2018:251–74.10.1016/B978-0-08-102015-9.00013-7Search in Google Scholar

[70] Minoshima M, Kikuchi K. Photostable and photoswitching fluorescent dyes for super-resolution imaging. J Biol Inorg Chem. 2017;22:639–52.10.1007/s00775-016-1435-ySearch in Google Scholar PubMed

[71] Uno K, Bossi ML, Konen T, Belov VN, Irie M, Hell SW. Asymmetric diarylethenes with oxidized 2-Alkylbenzothiophen-3-yl units: Chemistry, fluorescence, and photoswitching. Adv Opt Mater. 2019;7:1801746.10.1002/adom.201801746Search in Google Scholar

[72] Uno K, Bossi ML, Irie M, Belov VN, Hell SW. Reversibly photoswitchable fluorescent diarylethenes resistant against photobleaching in aqueous solutions. J Am Chem Soc. 2019;141:16471–8.10.1021/jacs.9b08748Search in Google Scholar PubMed

[73] Kathan M, Hecht S. Photoswitchable molecules as key ingredients to drive systems away from the global thermodynamic minimum. Chem Soc Rev. 2017;46:5536–50.10.1039/C7CS00112FSearch in Google Scholar PubMed

[74] Szymański W, Beierle JM, Kistemaker HA, Velema WA, Feringa BL. Reversible photocontrol of biological systems by the incorporation of molecular photoswitches. Chem Rev. 2013;113:6114–78.10.1021/cr300179fSearch in Google Scholar PubMed

[75] Zhang J, Wang J, Tian H. Taking orders from light: progress in photochromic bio-materials. Mater Horiz. 2014;1:169–84.10.1039/C3MH00031ASearch in Google Scholar

[76] Xiao C, Zhao W-Y, Zhou D-Y, Huang Y, Tao Y, Wu W-H, et al. Recent advance of photochromic diarylethenes-containing supramolecular systems. Chin Chem Lett. 2015;26:817–24.10.1016/j.cclet.2015.05.013Search in Google Scholar

[77] Lerch MM, Hansen MJ, van Dam GM, Szymanski W, Feringa BL. Emerging targets in photopharmacology. Angew Chem Intl Edn. 2016;55:10978–99.10.1002/anie.201601931Search in Google Scholar PubMed

[78] Reeßing F, Szymanski W. Beyond photodynamic therapy: light-activated cancer chemotherapy. Curr Med Chem. 2017;24:4905–50.10.2174/0929867323666160906103223Search in Google Scholar PubMed

[79] Velema WA, Szymanski W, Feringa BL. Photopharmacology: beyond proof of principle. J Am Chem Soc. 2014;136:2178–91.10.1021/ja413063eSearch in Google Scholar PubMed

[80] Presa A, Brissos RF, Cabellero AB, Borilovic I, Korrodi-Gregório L, Pérez-Tomás R, et al. Photoswitching the cytotoxic properties of platinum(II) compounds. Angew Chem Intl Edn. 2015;54:4561–5.10.1002/anie.201412157Search in Google Scholar PubMed

[81] Albert L, Vázquez O. Photoswitchable peptides for spatiotemporal control of biological functions. Chem Commun. 2019;55:10192–213.10.1039/C9CC03346GSearch in Google Scholar

[82] Babii O, Afonin S, Garmanchuk LV, Nikulina VV, Nikolaienko TV, Storozhuk OV, et al. Direct photocontrol of peptidomimetics: an alternative to oxygen-dependent photodynamic cancer therapy. Angew Chem. 2016;128:5583–6.10.1002/ange.201600506Search in Google Scholar

[83] Babii O, Afonin S, Ischenko AY, Schober T, Negelia AO, Tolstanova GM, et al. Structure-activity relationships of photoswitchable diarylethene-based β-hairpin peptides as membranolytic antimicrobial and anticancer agents. J Med Chem. 2018;61:10793–813.10.1021/acs.jmedchem.8b01428Search in Google Scholar PubMed

[84] Schober T, Wehl I, Afonin S, Babii O, Iampolska A, Schepers U, et al. Controlling the uptake of diarylethene-based cell-penetrating peptides into cells using light. ChemPhotoChem. 2019;3:384–91.10.1002/cptc.201900019Search in Google Scholar

[85] Fleming C, Remón P, Li S, Simeth NA, König B, Grøtli M, et al. On the use of diarylmaleimide derivatives in biological contexts: An investigation of the photochromic properties in aqueous solution. Dyes Pigm. 2017;137:410–20.10.1016/j.dyepig.2016.10.023Search in Google Scholar

[86] Komarov IV, Afonin S, Babii O, Schober T, Ulrich AS. Efficiently photocontrollable or not? Biological activity of photoisomerizable diarylethenes. Chem Eur J. 2018;24:11245–54.10.1002/chem.201801205Search in Google Scholar PubMed

[87] Higashiguchi K, Taira G, Kitai J-I, Hirose T, Matsuda K. Photoinduced macroscopic morphological transformation of an amphiphilic diarylethene assembly: reversible dynamic motion. J Am Chem Soc. 2015;137:2722–9.10.1021/ja512924qSearch in Google Scholar PubMed

[88] Kobatake S, Takami S, Muto H, Ishikawa T, Irie M. Rapid and reversible shape changes of molecular crystals on photoirradiation. Nature. 2007;446:778–81.10.1038/nature05669Search in Google Scholar PubMed

[89] Nakagawa Y, Morimoto M, Yasuda N, Hyodo K, Yokojima S, Nakamura S, et al. Photosalient effect of diarylethene crystals of Thiazolyl and Thienyl derivatives. Chem Eur J. 2019;25:7874–80.10.1002/chem.201900811Search in Google Scholar PubMed

[90] Mamiya J-I, Kuriyama A, Yokota N, Yamada M, Ikeda T. Photomobile polymer materials: photoresponsive behavior of cross-linked liquid-crystalline polymers with mesomorphic diarylethenes. Chem Eur J. 2015;21:3174–7.10.1002/chem.201406299Search in Google Scholar PubMed

[91] Kuenstler AS, Hayward RC. Light-induced shape morphing of thin films. Curr Opinion Colloid Interface Sci. 2019;40:70–86.10.1016/j.cocis.2019.01.009Search in Google Scholar