Monophilic Liquid Crystals derived from Sugars
Sugars are very suitable source for monophilic liquid crystals.
They have strong chirality fixed in rigid rings leading to unusual chirality effects of the mesophases (helical inversions,
TGBA phases, reentrant cholesteric and reentrant TGBA phases, etc.).
They exist in big varity of diastereomers allowing an efficient fine tuning of the physical properties.
They are very easy accessible. This allows new technical applications like color pigments.
Our carbohydrate liquid crystals are now used for the new BASF printing colors : Ultraking Paliocolor®.
Rainbow colors are reflected at the helical pitch of the cholesteric phase. The observed color depends on the viewing angle, e.g. the beatle looks green and blue.
Helical twisting power of carbohydrate derivatives
V. Vill, F. Fischer and J. Thiem
Z. Naturforsch. 43a, 1119-1125 (1988).
Ferroelectric liquid crystal mixtures with carbohydrate derivatives as
dopants
V. Vill, F. Fischer and J. Thiem
Z. Naturforsch. 44a, 675-679 (1989).
Synthesis and properties of calamitic liquid crystals from deoxygenated
carbohydrate derivatives
P. Pudlo, J. Thiem and V. Vill
Chem. Ber. 123, 1129-1135 (1990).
Discotic Peracylated Glycosides
V. Vill and J. Thiem
Liq. Cryst. 9, 451-455 (1991).
The Use of Simple Sugars for the Synthesis of Chiral Monophilic Liquid Crystals
V. Vill, F. Bachmann, I. Pelyvás, P. Pudlo and J. Thiem
Mol. Cryst. Liq. Cryst. 213, 57-65 (1992).
First Observation of Selective Reflection and Blue Phases in Chiral Discotic Liquid Crystals
D. Krüerke, H.-S. Kitzerow, G. Heppke and V. Vill
Ber. Bunsen-Ges. Phys. Chem. 97, 1371-1375 (1993).
Use of chiral group 4-hydroxyl-1-alkyl-2,3,5-tridesoxy-á-D-glyceropento-pyranoside for production of polar, liquid-crystal material
P. Delavier, K. Siemensmeyer, V. Vill and A. Hartwig
German Patent DE 4.316.826.4 (19.5.93/24.11.94); Chem. Abstr. 122, 278274.
Sign Inversion of the Helical Pitch in Carbohydrate-based Liquid Crystals
V. Vill, H.-W. Tunger, H. Stegemeyer and K. Diekmann
Tetrahedron Asymmetry 5, 2443-2446 (1994).
Chiral dihydropyranyl benzoates and tetrahydropyranyl benzoates as liquid crystal dopants
P. Delavier, K. Siemensmeyer, V. Vill, A. Hartwig, G. Gesekus and H.-W. Tunger
Eur. Pat. Appl. EP 630.892 (13.05.1994/28.12.1994), 12 pp; Chem. Abstr. 123, 112073.
A new homologous series of liquid crystals with a reentrente TGB-A phase
V. Vill and H.-W. Tunger
J. Chem. Soc., Chem. Commun. 1047-1048 (1995).
Liquid Crystals Derived from Carbohydrates: Synthesis and Properties of Oxadecaline Compounds
V. Vill and H.-W. Tunger
Liebigs Ann. 1055-1059 (1995).
Sign inversion of the spontaneous polarisation in induced liquid crystalline smectic-C* phases
H. Stegemeyer, A. Sprick, M.V. Osipov, V. Vill and H.-W. Tunger
Phys. Rev. E51, 5721-5724 (1995).
The Use of Glucose as a Trifunctional Building Block for Chiral Liquid Crystals
V. Vill, H.-W. Tunger and M. Paul
J. Mater. Chem. 5, 2283-2290 (1995).
Polymerisierbare chirale Verbindungen und deren Verwendung
K.-H. Etzbach, P. Delavier, K. Siemensmeyer, G. Wagenblast, L. Laupichler and V. Vill
Ger. Offen. DE-OS 4.342.280 (11.12.1993/14.06.1995), 18 pp; Chem. Abstr. 123, 83352.
Chiral compounds"
K. Siemensmeyer, V. Vill, and H.-W. Tunger
Ger. Offen. DE-OS 4.408.804 (15.03.1994/21.09.1995), 8 pp.; Chem. Abstr. 124, 41495.
Thermochromic coatings
M. Gailberger, A. Barth, H.R. Kricheldorf, V. Vill, M. Gurau and M. Berghahn
Ger. Offen. DE-OS 4.416.993 (13.05.94/16.11.95); Eur. Pat. Appl. EP 682.092 (1.4.95/15.11.95), 18 pp.; Chem. Abstr. 124, 120282.
Glucose: ein idealer Grundstoff für monophile Flüssigkristalle
V. Vill and H.-W. Tunger
Perspektiven nachwachsendender Rohstoffe in der Chemie, Editor H. Eierdanz, VCH Verlag Chemie, 1996, p. 299-303.
Cholesteric helix inversion: Novel nitro compounds showing unusual changes of the cholesteric helical pitch
Liq. Cryst. 20, 449-452 (1996).
Structural Variation of Liquid Crystalline Trioxadecalines
V. Vill, H.-W. Tunger and M. von Minden
J. Mater. Chem. 6, 739-745 (1996).
Re-entrant and induced mesophases: Mixed systems showing re-entrant TGBA and re-entrant cholesteric phases
V. Vill, H.-W. Tunger and D. Peters
Liq. Cryst. 20, 547-552 (1996).
Ferroelectric Liquid Crystals based on Carbohydrates
V. Vill, H.-W. Tunger and A. Borwitzky
Ferroelectrics 180, 227-231 (1996).
Chiral compounds and their uses
K. Siemensmeyer, V. Vill, H.-W. Tunger and M. Paul
Ger. Offen. DE 4.442.614 (30.11.94); Eur. Pat. Appl. EP 714.904 (21.11.95), publ. 5.6.96.
Cholesteric helix inversion: Investigations on the influence of terminal group on the inversion of the helical pitch in trioxadecalins
V. Vill, M. von Minden and D. Bruce
J. Mater. Chem. 7, 893-899 (1997).
Synthesis of Chiral Liquid Crystals with a Bisubstituted Tetrahydropyran Ring
A. Borwitzky, G. Gesekus and V. Vill,
Proc. SPIE-Int. Soc. Opt. Eng. 3319, 105-108 (1998).
Chiral effects in trioxadecalin derived liquid crystals
V. Vill, H. M. von Minden, D. Sinou, C. Moineau, V. Bolitt
Proc. SPIE-Int. Soc. Opt. Eng. 3319, 109-112 (1998).
Liquid Crystalline Trioxadecalins: The Mesogenic Chirality as Sensor for Molecular Conformation and
Orientation
V. Vill, B. Bertini, D. Sinou
ACS Sym. Ser. 798, 206-213, 2001.
Stereospecific synthesis of new trioxadecalin derived liquid crystals bearing halogen substituents on the phenyl
ring
B. Bertini, C. Moineau, D. Sinou, G. Gesekus, V.Vill
Eur. J. Org. Chem. 375-381 (2001).
Enantiopure trioxadecalin derived liquid crystals: influence of phenyl substitution on the mesogenic
properties
B. Bertini, C. Moineau, D. Sinou, V.Vill
J. Carbohydr. Chem. 315-327 (2001).
Chiral 1,3-dioxanes
F. Prechtl, S. Haremza, F. Meyer, R. Parker, K. Kürschner, V. Vill, M.
Paul
Eur. Pat. Appl. EP 1.136.478 (08.03.2001/26.09.2001).
Amphiphilic Liquid Crystals Derived from Carbohydrates
The simplest way to make liquid crystals from sugars are alkylated sugar.
The amphiphilic character causes the mesomorphic properties.
This mesogenes can have surfactant properties.
They have importants in biological systems.
And, they allow a well defined architecture of macroscopic ordered systems.
Our focus are glycolipids of plant membrans and the influence of the chemical configuration on membran fusion, endocytose
and cell-cell regognition processes.
Studies on liquid-crystalline glycosides
V. Vill, Th. Böcker, J. Thiem and F. Fischer
Liq. Cryst. 6, 349-356 (1989).
Flüssigkristalline 4,6-Alkylidenglucosen
J. Thiem, V. Vill, R. Miethchen and D. Peters
J. Prakt. Chem. 333, 173-175 (1991).
Liquid Crystalline 6-Desoxy Glycosides
V. Vill, T. Lindhorst and J. Thiem
J. Carbohydr. Chem. 10, 771-786 (1991).
Liquid Crystalline Glucamine Derivatives
V. Vill, H. Kelkenberg and J. Thiem
Liq. Cryst. 11, 459-467 (1992).
Enzymatic Synthesis of Discotic Liquid Crystals
V. Vill, B. Sauerbrei and J. Thiem
Liq. Cryst. 11, 949-952 (1992).
Synthesis and Properties of Sulfated Alkyl Glycosides
Th. Böcker, Th. K. Lindhorst, J. Thiem and V. Vill
Carbohydr. Res. 230, 245-256 (1992).
D-Galacturonsäurederivate mit flüssigkristallinen Eigenschaften
Ch. Vogel, U. Jeschke, V. Vill and H. Fischer
Liebigs Ann. Chem. 1171-1177 (1992).
A Carbohydrate with a Rectangular Discotic Phase
H. Fischer, V. Vill, V. Vogel and U. Jeschke
Liq. Cryst. 15, 733-737 (1993).
Liquid-Crystalline D-Glucose Dialkyl Acetals and Dodecyl D-Glucofuranosides
L.F. Tietze, K. Böge and V. Vill
Chem. Ber. 127, 1065-1068 (1994).
A note on the melting point of a-solanine - The solution of a riddle -
V. Grassert and V. Vill
Liquid Crystals Today 4 (1) 4-5 (1994).
Mesogenic Amino Sugars
P. Stangier, S. Rohde, V. Vill, J. Thiem and U. Jeschke
Liq. Cryst. 17, 589-595 (1994).
On the structure of the thermotropic cubic phase
S. Fischer, H. Fischer, S. Diele, G. Pelzl, K. Jankowsky, R.R. Schmidt and V. Vill
Liq. Cryst. 17, 855-861 (1994).
Thermotropic Liquid Crystals Based on Amphiphilic Carbohydrates
H. Prade, R. Miethchen and V. Vill
J. Prakt. Chem. 337, 427-440 (1995).
Mesomorphic Derivatives of the 6-Amino-6-deoxy-D-galactose
U. Jeschke, Ch. Vogel, V. Vill and H. Fischer
J. Mater. Chem. 5, 2073-2078 (1995).
Investigation of the influence of carbohydrate amphiphiles on the complex catalysed asymmetric hydrogenation of (Z)-methyl acetamidocinnamte in water
I. Grassert, V. Vill, G. Oehme
J. Mol. Catalysis A116, 231-236 (1997).
Thermotropic and lyotropic phase behaviour of monoalkyl glycosides
P. Sakya, J.M. Seddon and V. Vill
Liq. Cryst. 23, 409-424 (1997).
Thermotropic and lyotropic properties of long chain alkyl glycopyranosides, Part I: Monosaccharide headgroups
V. Vill, H.M. von Minden, M.H.J. Koch, U . Seydel, K. Brandenburg
Chem. Phys. Lipids 104, 75-91 (2000).
Preparation and characterization of new micelle-forming cholesterol
amphiphiles
D. Meißner, I. Grassert, G. Oehme, G. Holzhüter, V. Vill
Colloid Polym. Sci. 278, 364-368 (2000).
Thermotropic and lyotropic properties of long chain alkyl glycopyranosides, Part II: Disaccharide headgroups
H. M. von Minden, K. Brandenburg, U. Seydel, M. H. J. Koch
V. Garamus, R. Willumeit, V. Vill, Chem. Phys. Lipids 106, 157-179 (2000).
Conformatiotional and Thermal Phase Behavior of Oligomethylene Chains Constrained by Carbohydrate Hydrogen-Bond
Networks
M. Masuda, V. Vill, T. Shimizu
J. Am. Chem. Soc. 122, 12327-12333 (2000)
Helical Twisting Power of Glycolipids in Lyotropic Cholesteric Phases
K. Hiltrop, M. von Minden, M. Pape, V. Vill
J. Colloid Interf. Sci. 236, 108-115 (2001).
Synthesis and mesogenic properties of glycosyl diacylglycerols
H. M. von Minden, M. Morr, G. Milkereit, E. Heinz, V. Vill
Chem. Phys. Lipids 114, 55-80 (2002).
Carbohydrate liquid crystals: structure/property relationship of
thermotropic and lyotropic glycolipids
V. Vill, R. Hashim
Curr. Opinion Colloid Interf. Sci. 7, 395-409 (2002).
Effects of carbohydrate headgroups on the stability of induced cubic phases in binary mixtures of
glycolipids
H. M. von Minden, G. Milkereit, V. Vill
Chem. Phys. Lipids 120, 45-56 (2002).
Synthesis of Branched-Chain Alkyl Glucosides and Their Liquid Crystal
Behaviour
H. Hassan , A. Sazali Hamzah , V. Vill , M. Wulf
electronic-Liquid Crystal Communications, 2003/Feb/05 07:19:24, 2003
http://www.e-lc.org/.
Lipids and Steroids
Lipids like paraffins give ordered phases like smectic B. Steroids are special class of chiral lipids, which give less ordered phases and smectic A phases without phase separation. The relationship between thermotropic properties and biological functions is not clear yet. Steroids are a very suitable source for chiral liquid crystals.
Ferroelektrische Cholesterin-Derivate
V. Vill and J. Thiem
Z. Naturforsch. 45a, 1205-1210 (1990).
Steroidal ether lipids with liquid crystalline properties
V. Vill and N. Weber
Chem. Phys. Lipids 58, 105-110 (1991).
3b-Alkoxycholest-5-enes
V. Vill and N. Weber
Mol. Cryst. Liq. Cryst. Lett. 8, 49-51 (1991).
Flüssigkristalline aromatische Cholesterin-Derivate
V. Vill, J. Thiem and P. Rollin
Z. Naturforsch. 47a, 515-520 (1992).
Liquid Crystalline Cholestanyl and Cholesteryl Ether Lipids
V. Vill and N. Weber
Mol. Cryst. Liq. Cryst. 250, 73-83 (1994).
Use of chiral group R-(+)-3-oxyalkyl-cyclopentene for production of polar, liquid-crystal material
P. Delavier, K. Siemensmeyer, S. Rohde, V. Vill and N. Weber
German Patent DE 4.316.444.7 (19.5.93/24.11.94); Chem. Abstr. 122, 278273.
Synthesis and Photochemical Behaviour of 3-(Estran-16-yl)acrylates and 2-(Estran-16-yl)vinyl ketones
Thies Thiemann, Carolin Thiemann, Shinya Sasaki, Volkmar Vill, Shuntaro Mataka and Masashi Tashiro
J. Chem. Res. (S) 248-249, (M) 1736-1750 (1997).
Liquid Crystals with Aliphatic Rings
The study of aliphatic rings can be used to quantify the influence of the conformation and global molecular shape on mesogenic properties.
Synthesis, Properties and Conformations of Liquid Crystalline 1,4-Dioxanes and Comparison with the Corresponding 1,4-Dithian, Cyclohexane, and Benzene Derivatives
J. Thiem, V. Vill and F. Fischer
Mol. Cryst. Liq. Cryst. 170, 43-51 (1989).
Flüssigkristalle mit monosubstituierten aliphatischen Ringen
V. Vill and J. Thiem
Z. Naturforsch. 45a, 1345-1348 (1990).
Correlation of Liquid Crystalline Properties and Molecular Conformations of Series of Homologue Dioxanes
V. Vill and J. Thiem
Mol. Cryst. Liq. Cryst. Lett. 8, 27-32 (1991).
Liquid crystalline bicyclopentanes
Armin de Meijere, Matthias Messner and Volkmar Vill
Mol. Cryst. Liq. Cryst. 257, 161-167 (1994).
Synthesis and liquid crystalline properties of 5-alkyl-1,4-dioxane-2-carboxylic
esters
M. Braun, B. Spieker, A. Hahn, V. Vill
Synthesis 2129-2137 (2002).
New Liquid Crystalline Materials for Various Applications
Synthesis and Properties of Bis(5-alkoxytropolonato) Metallomesogens
A. Mori, M. Takemoto, R. Mori, H. Takeshita, S. Ujiie
Chem. Lett. 601-602 (1998).
New Twin-Type Troponoid Liquid Crystals with a Smectic C Phase
A. Mori, M. Takemoto, V. Vill
Chem. Lett. 617-618 (1998).
Convergent Synthesis of Columnar Twins and Tetramers from Triphenylene Building Blocks. The First Example of a Columnar Spiro-Twin
J.L. Schulte, S. Laschat, V. Vill, E. Nishikawa, H. Finkelmann, M. Nimtz
Eur. J. Org. Chem. 2499-2506 (1998).
Mesogenic Properties of Bis(5-Alkoxytropolonato)Metals
A. Mori, M. Takemoto, R. Mori, H. Takeshita, S. Ujiie, V. Vill
Mol. Cryst. Liq. Cryst. 332, 127-134 (1999).
Hexakis(terthiophenylthio)benzene as a New Class of Liquid Crystalline Molecule
S. Inoue, S. Nishiguchi, S. Murakami, Y. Aso, T. Otsubo, V. Vill, A. Mori, S. Ujiie
J. Chem. Res. (S) 596-597 (1999).
An Optically Active Diarylethene Having Cholesterol Units: A Dopant for Photoswitching of Liquid Crystal Phases
K. Uchida, Y. Kawai, Y. Shimizu, V. Vill, M. Irie
Chem. Lett. 654-655 (2000).
Dimeric liquid crystals with two troponoid mesogenic moieties: effect of the direction of the carbonyl group on the mesomorphic
properties
M. Takemoto, A. Mori, S. Ujiie, V. Vill
Liq. Cryst. 29, 687-695 (2002).
Novel nitronyl nitroxides: synthesis and properties
S. Greve, V. Vill, W. Friedrichsen
Z. Naturforsch. 57c, 677-684 (2002).
LiqCryst
The statistical analysis of mesogenic properties allows the quantification of structure-property-relationships. The goal is the prediction of physical properties from the chemical structure.
LiqCryst - Database of Liquid Crystalline Compounds
LiqCryst News Letter, Issue 3/97
Landolt-Börnstein, New Series, Vol. IV/7 "Liquid Crystals", Subvol. IV/7a to IV/7f
Transition Temperatures and Related Properties of Mesogenic Compounds
V. Vill, Springer-Verlag, Berlin, 1992-1997.
LiqCryst 2.1 - Liquid Crystal Database
V. Vill
Fujitsu Kyushu System (FQS) Ltd, Fukuoka, Japan, 1996;
LCI Publisher, Hamburg, 1996.
LiqCryst for Polymers 2.1
V. Vill
LCI Publisher, Hamburg, 1996.
LiqCryst 3.0 - Liquid Crystal Database
V. Vill
Fujitsu Kyushu System (FQS) Ltd, Fukuoka, Japan, 1997;
LCI Publisher, Hamburg, 1997.
LiqCryst for Polymers 3.0
V. Vill
LCI Publisher, Hamburg, 1997.
Conception and Realization of the Liquid Crystal Database LiqCryst
V. Vill
Liq. Cryst. Today 5 (3) 6-7 (1995).
Predicting the transition temperature of smectic liquid crystalline
compounds from their structure using artifical neural networks
R. Schröder, H. Kränz, V. Vill, B. Meyer
J. Chem. Soc., Perkin Trans. 2, 1685-1689
(1996).
A New Database in the Material Sciences
V. Vill and Th. Thiemann
GIT Labor-Fachzeitschrift 40, 1236-1237 (1996).
Prediction of Material Properties from the Chemical Structures. The Clearing
Temperature of Nematic Liquid Crystals Derived from their Chemical
Structures by Artifical Neural Networks
H. Kränz, V. Vill, B. Meyer
J. Chem. Inf. Comput. Sci., 36, 1173-1177 (1996).
LiqCryst: Database of Liquid Crystalline Compounds for Personal Computers
Volkmar Vill
Software-Entwicklung in der Chemie 10 (Ed. J. Gasteiger), GDCh, Frankfurt, p. 155-158 (1996).
Development of an incremental system for the prediction of the nematic-isotropic phase transition temperature of liquid crystals with two aromatic rings
Th. Thiemann, and V. Vill
Liq. Cryst. 22, 519-523 (1997).
Homologous Series of Liquid Crystalline Steroidal Lipids
T. Thiemann and V. Vill
J. Phys. Ref. Chem. Data 26, 291-333 (1997).
Vorhersage der Umwandlungstemperaturen flüssigkristalliner Verbindungen
V. Vill and D. Peters
Chemie und Informatik: Terra incognita oder das Land der unbegrenzten M&oouml;glichkeiten ?, Shaker Verlag, Aachen, Editor: B. Koppenhoefer and U. Epperlein, 1997.
LiqCryst 2.1: database and scientific tool
V. Vill, H. Sajus, and T. Thiemann
Proc. SPIE-Int. Soc. Opt. Eng. 3318, 160-162 (1998).
Prediction of phase transition temperatures of liquid crystals with the help of a similarity concept
V. Vill and D. Peters
Proc. SPIE-Int. Soc. Opt. Eng. 3319, 74-77 (1998).
LiqCryst im WebDoc
General Aspects of Liquid Crystal Research
Handbook of Liquid Crystals, Vol. 1, 2a, 2b and 3
D. Demus, J.W. Goodby, G.W. Gray, H.W. Spiess, V. Vill (Editors)
VCH Verlag, Weinheim, 1998.
General Synthetic Strategies
Thies Thiemann and Volkmar Vill
Handbook of Liquid Crystals, Vol. 1, Chapter 4, p. 87-113, 1998.
Amphotropic Liquid Crystals
D. Blunk, K. Praefcke and V. Vill
Handbook of Liquid Crystals, Vol. 3, Chapter 6, p. 305-340, 1998.
Physical Properties of Liquid Crystals
D. Demus, J.W. Goodby, G.W. Gray, H.W. Spiess, V. Vill (Editors)
Wiley-VCH, Weinheim, 1999.
Structure/Property Relationship of Liquid Crystals
V. Vill, A. Mori
Japanese Handbook of Liquid Crystals, Maruzen, Tokyo, Chapter 3.2, p. 267-280,
2000.
Carbohydrate Liquid Crystals
V. Vill, T. Kato
Japanese Handbook of Liquid Crystals, Maruzen, Tokyo, Chapter 3.9.3, p. 432-438,
2000.
Chemical Structures and Polymorphism
V. Vill
in "Chirality in Liquid Crystals", Ed. H. Kitzerow, Ch. Bahr, Springer-Verlag, New York,
2001.
Molecular Design of Liquid Crystals: Calamitics
V. Vill
in: Encyclopedia of Materials: Science and Technology, Elsevier Science, p. 4545-4551,
2001.
Landolt-Börnstein, New Series, Vol. VIII/5: Physical Properties of
Liquid Crystals, Subvol. VIII/5A
S. Pestov, Ed.: V. Vill
Springer-Verlag, Berlin, 2003.
History of Liquid Crystals
Early History of Liquid Crystalline Compounds
V. Vill
Mol. Cryst. Liq. Cryst. 213, 67-71 (1992);
Condens. Matter News. 1 (5) 25-28 (1992).
The Development of Liquid Crystal Research
V. Vill
Adv. Mater. 6, 527-528 (1994).
Vorländer's Wheel
D.W. Bruce, K. Heyns and V. Vill
Liq. Cryst. 23, 813-819 (1997).
Grey Levels in the History of Liquid Crystals
V. Vill
Liq. Cryst. 24, 21-24 (1998).
Chemical Information Systems
SciDex is a new software system which can organize all scientific data, information and knowledge.
SciDex has an object oriented database engine which was developed from the experiences of LiqCryst.
SciDex - the Scientific
Data Explorer
Recent application of the SciDex software systems are the
Landolt-Börnstein: Index of Organic Compounds, Subvol A, B and C
V. Vill, G. Peters, H. Sajus
Springer-Verlag, Berlin, 1999-2001.
Landolt-Börnstein: Index of Organic Compounds, Subvol D, E and F
Ch. Bauhofer, V. Vill, P.Weigner
Springer-Verlag, Berlin, 2002-2004.