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2 Liquid crystals are states (or compounds) having both fluidity like liquids and long range order like crystals. To be specific, liquid crystalline states involve an ordered molecular orientation but they partially or fully lack positional orders of gravity center in the arranged molecules compared to normal crystal states. Thermotropic and lyotropic liquid crystals are two main classes of liquid crystals. The former liquid crystalline phase appears by changing temperature, and the latter phase appears by changing solution concentration of amphiphilic compounds, etc. found in ) Most thermotropic liquid crystalline molecules have either a calamitic or discotic molecular shape. alamitic liquid crystals usually exhibit several mesophases: nematic, smectic, and cholesteric phases. orming these liquid crystalline states enables these compounds to exhibit characteristic functions such as optical anisotropy and ferroelectricity. Besides calamitic and discotic liquid crystals, other liquid crystals with unique molecular shapes e.g. banana-shaped ones with bent-cores 1,2) and shuttlecockshaped fullerene derivatives 3) have been investigated extensively. (a) Nematic Phase (b) Smectic Phase The nematic phase is a state in which molecules are oriented along the direction of the molecular long axis but the molecular gravity centers are randomly located like an isotropic liquid (ig. 1(a)). A nematic phase usually appears at a higher temperature than the other mesophases when there are several possible ones. The TN (Twisted Nematic) mode 4) of liquid crystal displays requires fast responding nematic liquid crystal molecules having large dielectric constant anisotropy, e.g. 5B (4-yano-4 -pentylbiphenyl). The smectic phases show a positionally ordered molecular arrangement with organization along the molecular long axis as well as with layered organizations shown in ig. 1(b). These phases appear at the lower temperature range with lower fluidity than those of nematic phases. Smectic phases are diverse due to a distinct molecular arrangement in the layers and distinct orders of inter- and intra- layers. The cholesteric phase shown in ig. 1(c) usually involves cholesteryl compounds. n the basis of chirality of the molecules, the phase demonstrates twisted molecular arrangements, resulting in helical structures with certain periodicity (pitch). The phase may be categorized into nematic phases and called a chiral nematic phase. An addition of chiral inducers into nematic liquid crystals also provides the cholesteric phase. Since the helical pitch is thermally responsive to changing reflective colors, they are applicable for liquid crystal thermometers. The discotic phases, the state composed by disk-like molecules (ig. 1(d)), are divided into more specific ones such as discotic nematic and discotic columnar types according to the molecular arrangements. It is a relatively new liquid crystalline phase initially (c) holesteric Phase (d) Discotic Phase (Discotic olumnar Phase (hexagonal)) ig. 1 Illustration of typical liquid crystal phases Liquid rystalline Phases with omplex 3D Structures Some mesophases with complex 3D molecular arrangements also have been discovered. ne representative example is the blue phase, which is expected to be a powerful candidate for fast response displays without an oriented film and a polarizer 6,7) and to be photonic crystals for laser oscillations. 8,9) Since the blue phases involve basic units, the so-called double-twist cylinders, all recognized phases, i.e., body centered cubic (Blue Phase I), simple cubic (Blue Phase II), and amorphous (Blue phase III) are optically isotropic. They are normally observed within a small temperature range (typically ~1 º) between cholesteric and isotropic phases. This fact has caused limitations on their application. In recent years, several research groups reported active examples e.g. extension of temperature range up to ~60 º by forming polymers in the blue phase (polymer-stabilized blue phase) 10) and up to ~40 º by developing two biphenyl-linked compounds. 11) 2

3 Polymer Dispersed Liquid rystals Polymer dispersed liquid crystals (PDL) are applied to smart windows which can switch the transparency of windows by turning voltage on and off. In the PDL films, liquid crystal domains are dispersed into the polymer matrix. Turning the voltage on can make the film transparent, because the refractive index of the liquid crystal domains becomes almost similar to that of the polymer matrix with respect to incident light by making liquid crystalline molecules align with the electric field. n the other hand, turning the voltage off makes the film translucent, because the refractive index of the liquid crystal becomes different from that of the matrix by forming a random location of the liquid crystalline molecules. In addition to the smart windows, the PDLs are also expected to be used as materials for reflective displays working with low power such as an electronic paper. Liquid rystalline Semiconductors There are many organic semiconductors having liquid crystallinity. Liquid crystalline semiconductors have provided much interest for enabling production of devices in a wet process at low cost, improvement of molecular orientation and carrier mobility utilizing their self-organizing ability in a post-process, and fabrication of flexible devices with high bending strength more than crystalline organic semiconductors. In addition to calamitic liquid crystalline semiconductors, 12) discotic ones have been developed. 13) The discotic liquid crystalline semiconductors demonstrate efficient carrier mobility along with the columnar direction of the stacked molecules, therefore, they can be used as materials for organic photovoltaics (PVs). 14) References 1) T. Niori, T. Sekine, J. Watanabe, T. urukawa,. Takezoe, J. Mater. hem. 1996, 6, ) D. Shen, A. Pegenau, S. Diele, I. Wirth,. Tschierske, J. Am. hem. Soc. 2000, 122, ) Y. Zhong, Y. Matsuo, E. Nakamura, J. Am. hem. Soc. 2007, 129, ) M. Schadt, W. elfrich, Appl. Phys. Lett. 1971, 18, ) S. handrasekhar, B. K. Sadashiva, K. A. Suresh, Pramana 1977, 9, ). Lee,. Park,. Kwon, S. J. Yun, J.. Park, S. ong, S. Shin, SID Symposium Digest of Technical Papers 2011, 42, ) M. Kimura, N. Nagumo, T. N. o, N. Endo,. Kikuchi, T. Akahane, pt. Mater. Express 2013, 3, ) W. ao, A. Muñoz, P. Palffy-Muhoray, B. Taheri, Nat. Mater. 2002, 1, ) K. Kim, S. ur, S. Kim, S. Jo, B. R. Lee, M.. Song, S. hoi, J. Mater. hem. 2015, 3, ). Kikuchi, M. Yokota, Y. isakado,. Yang, T. Kajiyama, Nat. Mater. 2002, 1, ). J. oles, M. N. Pivnenko, Nature 2005, 436, ). Iino, T. Usui, J. anna, Nat. ommun. 2015, ) S. Sergeyev, W. Pisula, Y.. Geerts, hem. Soc. Rev. 2007, 36, ).. esse, J. Weickert, M. Al-ussein, L. Dössel, X. eng, K. Müllen, L. Schmidt-Mende, Sol. Energy Mater. Sol. ells 2010, 94, ) K. Araya, A. Mukoh, T. Narahara,. Shirakawa, Synth. Met. 1986, 14, ) Y. Wan, D. Zhao, hem. Rev. 2007, 107, ) S. P. Yadav, S. Singh, Prog. Mater. Sci. 2016, 80, 38. Applications of Liquid rystal Media for Providing unctions Liquid crystals are also utilized as reaction media for providing some specific functions to other materials. A few decades ago, acetylene was polymerized in liquid crystal solvents to control the orientation of the polymer-aggregated fibril structure enhancing electrical conductivity to the oriented direction. 15) ther examples for such studies are synthesis of mesoporous silica in the reaction media composed of lyotropic liquid crystals 16) and realization of oriented carbon nanotubes in liquid crystal media. 17) 3

4 B4923 Nematic / Smectic Liquid rystals yanobiphenyls & Analogs 3 ( 2 ) 3 4B AS RN: ( 2 ) 4 3 ( 2 ) 5 3 ( 2 ) 6 5B AS RN: B AS RN: B AS RN: ( 2 ) 7 3 ( 2 ) 8 3 ( 2 ) 10 8B AS RN: B AS RN: B AS RN: ( 2 ) B AS RN: B AS RN: B AS RN: B ( 2 ) 3 3 ( 2 ) 4 3 ( 2 ) 5 4B AS RN: B AS RN: B AS RN: ( 2 ) 6 3 ( 2 ) 7 3 ( 2 ) 8 7B AS RN: B AS RN: B AS RN: ( 2 ) 9 3 ( 2 ) 11 10B AS RN: B AS RN: B AS RN: P1617 B4924 A ( 2 ) 3 3 ( 2 ) 4 4-(trans-4-Propylcyclohexyl)benzonitrile AS RN: (trans-4-Butylcyclohexyl)benzonitrile AS RN: (trans-4-Amylcyclohexyl)benzonitrile AS RN:

5 P ( 2 ) [trans-4-[(E)-1-Propenyl]cyclohexyl]benzonitrile AS RN: yano-4''-propyl-p-terphenyl AS RN: yano-4''-pentyl-p-terphenyl AS RN: A ( 2 ) 4 4'-(trans-4-Amylcyclohexyl)biphenyl-4-carbonitrile AS RN: D4909 T3318 luorinated Biphenyls & Analogs ,3-Difluoro-4-[(trans-4-propylcyclohexyl)methoxy]anisole AS RN: D ',3,4,5-Tetrafluoro-4''-propyl-1,1':4',1''-terphenyl AS RN: (2) '-luoro-4-pentyl-4''-propyl-1,1':4',1''-terphenyl AS RN: ,4-Difluoro-4'-(trans-4-ethylcyclohexyl)biphenyl AS RN: luoro-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: D4535 T3260 T ,4-Difluoro-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: ,4,5-Trifluoro-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: ',3,4,5-Tetrafluoro-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: E1158 D4534 E Ethoxy-2,3-difluoro-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: ( 2 ) 4 3,4-Difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl AS RN: trans,trans-4'-ethyl-4-(3,4,5-trifluorophenyl)bicyclohexyl AS RN: E1165 D4797 P trans,trans-4'-ethyl-4-(4-trifluoromethoxyphenyl)bicyclohexyl AS RN: trans,trans-4-(3,4-difluorophenyl)-4'-propylbicyclohexyl AS RN: trans,trans-4'-propyl-4-(3,4,5-trifluorophenyl)bicyclohexyl AS RN: E1157 B4925 D trans,trans-4-(4-ethoxy-2,3-difluorophenyl)- 4'-propylbicyclohexyl AS RN: ( 2 ) 3 trans,trans-4'-butyl-4-(3,4-difluorophenyl)bicyclohexyl AS RN: ( 2 ) 4 trans,trans-4-(3,4-difluorophenyl)-4'-pentylbicyclohexyl AS RN:

6 P2319 B4916 D ( 2 ) 4 trans,trans-4'-pentyl-4-(3,4,5-trifluorophenyl)bicyclohexyl AS RN: trans,trans-4'-(3-butenyl)-4-(3,4-difluorophenyl)bicyclohexyl AS RN: [Difluoro(3,4,5-trifluorophenoxy)methyl]- 4'-ethyl-3,5-difluorobiphenyl AS RN: D5130 T [Difluoro(3,4,5-trifluorophenoxy)methyl]- 3,5-difluoro-4'-propylbiphenyl AS RN: trans,trans-3,4,5-trifluoro- 4'-(4'-propylbicyclohexyl-4-yl)biphenyl AS RN: E1162 B4915 ther Biphenyls & Analogs Ethyl-4'-(trans-4-propylcyclohexyl)biphenyl AS RN: trans,trans-4'-(3-butenyl)-4-(p-tolyl)bicyclohexyl AS RN: P mg 3(2)4 ( 2) 4 3 (R)-1-Phenyl-1,2-ethanediyl Bis[4-(trans- 4-pentylcyclohexyl)benzoate] AS RN: E0257 A0608 arbonates ( 2 ) (4-Ethoxyphenoxycarbonyl)phenyl Ethyl arbonate AS RN: Amyl 4-(4-Ethoxyphenoxycarbonyl)phenyl arbonate AS RN: B1586 Phenyl Esters 3 ( 2 ) 6 2 ( 2 ) 2 4-yanophenyl 4-eptylbenzoate AS RN: yanophenyl 4-(3-Butenyloxy)benzoate AS RN: S0016 B0375 B1091 ( 2 ) ( 2 ) ( 2 ) 3 ( 2 ) ctylphenyl Salicylate AS RN: Ethoxyphenyl 4-Butylbenzoate AS RN: (exyloxy)phenyl 4-Butylbenzoate AS RN: B1092 P0896 P ( 2 ) 3 ( 2 ) ( 2 ) 4 ( 2 ) ( 2 ) 4 ( 2 ) n-ctyloxyphenyl 4-Butylbenzoate AS RN: Butoxyphenyl 4-Pentylbenzoate AS RN: exyloxyphenyl 4-Pentylbenzoate AS RN:

7 P0898 M ( 2 ) 4 ( 2 ) (2)53 3(2)5 4-n-ctyloxyphenyl 4-Pentylbenzoate AS RN: Methoxyphenyl 4-(3-Butenyloxy)benzoate AS RN: (S)-2-ctyl 4-[4-(exyloxy)benzoyloxy]benzoate AS RN: (2)53 3(2)5 (R)-2-ctyl 4-[4-(exyloxy)benzoyloxy]benzoate AS RN: M Schiff Bases 3 N N N 2 3 N-(4-Methoxybenzylidene)aniline AS RN: '-yanobenzylidene-4-ethoxyaniline AS RN: M0604 E0240 N N ( 2 ) N 3 2 N 4'-yanobenzylidene-4-butoxyaniline AS RN: [(4-Methoxybenzylidene)amino]benzonitrile AS RN: '-Ethoxybenzylidene-4-cyanoaniline AS RN: B0252 B ( 2 ) 3 N 3 ( 2 ) 4 N 3 ( 2 ) 5 N 4'-Butoxybenzylidene-4-cyanoaniline AS RN: '-(Amyloxy)benzylidene-4-cyanoaniline AS RN: '-exyloxybenzylidene-4-cyanoaniline AS RN: M0275 B0250 M N ( 2 ) N ( 2 ) N 3 N-(4-Methoxybenzylidene)-4-butylaniline AS RN: N-(4-Methoxy-2-hydroxybenzylidene)-4-butylaniline AS RN: N-(4-Methoxybenzylidene)-4-acetoxyaniline AS RN: M0602 B0255 E g 3 N N ( 2) N ( 2 ) 3 3 Ethyl 4-[(4-Methoxybenzylidene)amino]cinnamate AS RN: Butyl 4-[(4-Methoxybenzylidene)amino]cinnamate AS RN: '-Ethoxybenzylidene-4-butylaniline AS RN: E0254 B0372 M N 3 3 ( 2 ) 3 N 3 3 N N-(4-Ethoxybenzylidene)-4-acetylaniline AS RN: N-(4-Butoxybenzylidene)-4-acetylaniline AS RN: [(Methoxybenzylidene)amino]stilbene AS RN:

8 B N N 23 Terephthalbis(p-phenetidine) AS RN: A0554 A0683 D1094 Azoxybenzenes 3 N N 3 4,4'-Azoxydianisole D1096 AS RN: ,4'-Azoxydiphenetole D1093 N N 2 3 AS RN: N N ( 2 ) 3 N N ( 2 ) ( 2 ) 4 N N ( 2 ) 4 3 4,4'-Dipropoxyazoxybenzene AS RN: ,4'-Dibutoxyazoxybenzene AS RN: ,4'-Diamyloxyazoxybenzene AS RN: D1092 D1123 D mg 3 ( 2 ) 5 N N ( 2 ) ( 2 ) 7 N N ( 2 ) ( 2 ) 8 N N ( 2 ) 8 3 4,4'-Dihexyloxyazoxybenzene AS RN: ,4'-Di-n-octyloxyazoxybenzene AS RN: ,4'-Dinonyloxyazoxybenzene AS RN: D0553 A ( 2 ) 11 N N ( 2 ) NN 2 3 4,4'-Didodecyloxyazoxybenzene AS RN: holesteric Liquid rystals Diethyl Azoxybenzene-4,4'-dicarboxylate AS RN: holesteryl ompounds holesterol Acetate 0677 AS RN: holesterol Propionate AS RN: holesterol Butyrate AS RN: ( 2 ) 3 3 holesterol Valerate AS RN: ( 2 ) 4 3 holesterol exanoate AS RN: ( 2 ) 5 3 holesterol eptanoate AS RN: ( 2 ) 6 3 holesterol n-ctanoate AS RN:

9 N g ( 2 ) 7 3 holesterol Pelargonate AS RN: ( 2 ) 8 3 holesterol Decanoate AS RN: ( 2 ) 10 3 holesterol Laurate AS RN: ( 2 ) 12 3 holesterol Myristate AS RN: ( 2 ) 14 3 holesterol Palmitate AS RN: ( 2 ) 16 3 holesterol Stearate AS RN: holesterol ormate AS RN: g l holesterol hloroformate AS RN: holesterol ydrogen Succinate AS RN: g 500g ( 2 ) 7 ( 2 ) 7 3 holesterol leate AS RN: ( 2 ) 7 ( 2 ) 4 3 holesterol Linoleate AS RN: holesterol Benzoate AS RN: l l holesterol 2,4-Dichlorobenzoate AS RN: holesterol ydrocinnamate AS RN: holesterol ydrogen Phthalate AS RN: holesterol trans-innamate AS RN: holesterol Phenylacetate AS RN: Br holesteryl Bromide from Beef at AS RN: l holesteryl hloride AS RN: holesteryl arbonates holesterol Methyl arbonate AS RN: holesterol Ethyl arbonate AS RN:

10 (3)2 holesterol Isopropyl arbonate AS RN: (2)33 holesterol Butyl arbonate AS RN: holesterol Isobutyl arbonate AS RN: B (2)43 holesterol Amyl arbonate AS RN: (2)53 holesterol exyl arbonate AS RN: (2)63 holesterol eptyl arbonate AS RN: B ( 2) 7 3 holesterol n-ctyl arbonate AS RN: Discotic Liquid rystals (2)83 holesterol Nonyl arbonate AS RN: (2)5 3(2)5 (2)53 (2)53 (2)53 200mg (2)53 2,3,6,7,10,11-exakis(hexyloxy)triphenylene AS RN: (2) 8 ( 2) 7 3 holesterol leyl arbonate AS RN: ( 2) 7 3( 2) 7 (2)73 ( 2) 7 3 (2)73 200mg ( 2) 7 3 2,3,6,7,10,11-exakis[(n-octyl)oxy]triphenylene AS RN:

11 2036E