4-Cyano-4'-pentylbiphenyl

Last updated
4-Cyano-4'-pentylbiphenyl
4-Cyano-4'-pentylbiphenyl.svg
5CB-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
4′-Pentyl[1,1′-biphenyl]-4-carbonitrile
Other names
4'-Amyl-4-biphenylcarbonitrile, 4'-Pentyl-4-biphenylcarbonitrile, 4-Amyl-4'-cyanobiphenyl
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.050.068 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 255-093-2
PubChem CID
UNII
  • InChI=1S/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3 X mark.svgN
    Key: HHPCNRKYVYWYAU-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C18H19N/c1-2-3-4-5-15-6-10-17(11-7-15)18-12-8-16(14-19)9-13-18/h6-13H,2-5H2,1H3
    Key: HHPCNRKYVYWYAU-UHFFFAOYAV
  • N#Cc2ccc(c1ccc(cc1)CCCCC)cc2
Properties
C18H19N
Molar mass 249.357 g·mol−1
AppearanceColorless if isotropic or cloudy white if nematic
Density 1.022 g/cm3 [1]
Melting point 22.5 [1]  °C (72.5 °F; 295.6 K)
n// = 1.71, n = 1.53 [1]
Viscosity 28 mPa·s [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

4-Cyano-4'-pentylbiphenyl is a commonly used nematic liquid crystal with the chemical formula C18H19N. It frequently goes by the common name 5CB. 5CB was first synthesized by George William Gray, Ken Harrison, and J.A. Nash at the University of Hull in 1972 and at the time it was the first member of the cyanobiphenyls. [2] [3] The liquid crystal was discovered after Gray's group received a grant from the UK Ministry of Defence to find a liquid crystal that had liquid crystal phases near room temperature with the specific intention of using them in liquid crystal displays. The molecule is about 20 Å long. The liquid crystal 5CB undergoes a phase transition from a crystalline state to a nematic state at 22.5 °C and it goes from a nematic to an isotropic state at 35.0 °C. [1]

Contents

Production

5CB is produced by modifying biphenyl in a linear manner. First Br2 is added to the biphenyl to introduce a bromine atom to the end of the moiety. Next aluminium chloride and C4H9COCl is added to the sample, followed by the addition of potassium hydroxide and NH2NH2. By this point the molecule will have a bromine atom on one end of the rigid core and C5H11 on the other end. Finally, introduction of copper(I) cyanide and DMF results in the removal of the bromine and its replacement with CN, yielding 5CB. [3]

Related Research Articles

<span class="mw-page-title-main">Liquid-crystal display</span> Display that uses the light-modulating properties of liquid crystals

A liquid-crystal display (LCD) is a flat-panel display or other electronically modulated optical device that uses the light-modulating properties of liquid crystals combined with polarizers. Liquid crystals do not emit light directly but instead use a backlight or reflector to produce images in color or monochrome.

<span class="mw-page-title-main">Liquid crystal</span> State of matter with properties of both conventional liquids and crystals

Liquid crystal (LC) is a state of matter whose properties are between those of conventional liquids and those of solid crystals. For example, a liquid crystal can flow like a liquid, but its molecules may be oriented in a common direction as in solid. There are many types of LC phases, which can be distinguished by their optical properties. The contrasting textures arise due to molecules within one area of material ("domain") being oriented in the same direction but different areas having different orientations. An LC material may not always be in an LC state of matter.

<span class="mw-page-title-main">State of matter</span> Distinct forms that matter take on

In physics, a state of matter is one of the distinct forms in which matter can exist. Four states of matter are observable in everyday life: solid, liquid, gas, and plasma. Many intermediate states are known to exist, such as liquid crystal, and some states only exist under extreme conditions, such as Bose–Einstein condensates and Fermionic condensates, neutron-degenerate matter, and quark–gluon plasma. For a list of exotic states of matter, see the article List of states of matter.

<span class="mw-page-title-main">London dispersion force</span> Cohesive force between species

London dispersion forces are a type of intermolecular force acting between atoms and molecules that are normally electrically symmetric; that is, the electrons are symmetrically distributed with respect to the nucleus. They are part of the van der Waals forces. The LDF is named after the German physicist Fritz London. They are the weakest intermolecular force.

A mesogen is a compound that displays liquid crystal properties. Mesogens can be described as disordered solids or ordered liquids because they arise from a unique state of matter that exhibits both solid- and liquid-like properties called the liquid crystalline state. This liquid crystalline state (LC) is called the mesophase and occurs between the crystalline solid (Cr) state and the isotropic liquid (Iso) state at distinct temperature ranges.

In chemistry, an interhalogen compound is a molecule which contains two or more different halogen atoms and no atoms of elements from any other group.

A biaxial nematic is a spatially homogeneous liquid crystal with three distinct optical axes. This is to be contrasted to a simple nematic, which has a single preferred axis, around which the system is rotationally symmetric. The symmetry group of a biaxial nematic is i.e. that of a rectangular right parallelepiped, having 3 orthogonal axes and three orthogonal mirror planes. In a frame co-aligned with optical axes the second rank order parameter tensor of a biaxial nematic has the form

<span class="mw-page-title-main">Biphenyl</span> Chemical compound

Biphenyl is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen may use the prefixes xenyl or diphenylyl.

<span class="mw-page-title-main">Twisted nematic field effect</span> Type of thin-film-transistor liquid-crystal display technology

The twisted nematic effect (TN-effect) was a main technology breakthrough that made LCDs practical. Unlike earlier displays, TN-cells did not require a current to flow for operation and used low operating voltages suitable for use with batteries. The introduction of TN-effect displays led to their rapid expansion in the display field, quickly pushing out other common technologies like monolithic LEDs and CRTs for most electronics. By the 1990s, TN-effect LCDs were largely universal in portable electronics, although since then, many applications of LCDs adopted alternatives to the TN-effect such as in-plane switching (IPS) or vertical alignment (VA).

<span class="mw-page-title-main">George Gray (chemist)</span>

George William Gray was a Professor of Organic Chemistry at the University of Hull who was instrumental in developing the long-lasting materials which made liquid crystal displays possible. He created and systematically developed liquid crystal materials science, and established a method of practical molecular design. Gray was recipient of the 1995 Kyoto Prize in Advanced Technology.

<span class="mw-page-title-main">Martin Schadt</span> Swiss physicist and inventor (born 1938)

Martin Schadt is a Swiss physicist and inventor.

<span class="mw-page-title-main">Lyotropic liquid crystal</span>

Lyotropic liquid crystals result when fat-loving and water-loving chemical compounds known as amphiphiles dissolve into a solution that behaves both like a liquid and a solid crystal. This liquid crystalline mesophase includes everyday mixtures like soap and water.

<span class="mw-page-title-main">Mesophase</span>

In chemistry and chemical physics, a mesophase or mesomorphic phase is a phase of matter intermediate between solid and liquid. Gelatin is a common example of a partially ordered structure in a mesophase. Further, biological structures such as the lipid bilayers of cell membranes are examples of mesophases. Mesophases with long-range positional order but no orientational order are plastic crystals, whereas those with long-range orientational order but only partial or no positional order are liquid crystals.

A blue phase mode LCD is a liquid crystal display (LCD) technology that uses highly twisted cholesteric phases in a blue phase. It was first proposed in 2007 to obtain a better display of moving images with, for example, frame rates of 100–120 Hz to improve the temporal response of LCDs. This operational mode for LCDs also does not require anisotropic alignment layers and thus theoretically simplifies the LCD manufacturing process.

There are various classifications of the electro-optical modes of liquid crystal displays (LCDs).

<span class="mw-page-title-main">Sivaramakrishna Chandrasekhar</span> Indian physicist (1930-2004)

Sivaramakrishna Chandrasekhar FNA, FRS was an Indian physicist who won the Royal Medal in 1994. He was the founder-president of the International Liquid Crystal Society.

A liquid-crystal laser is a laser that uses a liquid crystal as the resonator cavity, allowing selection of emission wavelength and polarization from the active laser medium. The lasing medium is usually a dye doped into the liquid crystal. Liquid-crystal lasers are comparable in size to diode lasers, but provide the continuous wide spectrum tunability of dye lasers while maintaining a large coherence area. The tuning range is typically several tens of nanometers. Self-organization at micrometer scales reduces manufacturing complexity compared to using layered photonic metamaterials. Operation may be either in continuous wave mode or in pulsed mode.

<span class="mw-page-title-main">Antal Jákli</span> Hungarian-American physicist (born 1956)

Antal I. "Tony" Jákli is a Hungarian-American physicist and professor of chemical physics at Kent State University. He is known for his work with bent-core, flexoelectric, and ferroelectric liquid crystals.

<span class="mw-page-title-main">N. V. Madhusudana</span> Indian physicist (born 1944)

Nelamangala Vedavyasachar Madhusudana is an Indian physicist and an emeritus scientist at Raman Research Institute. Known for his research on liquid crystals, Madhusudhana is an elected fellow of Indian Academy of Sciences and Indian National Science Academy. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, for his contributions to physical sciences in 1989.

<span class="mw-page-title-main">Yuriy Reznikov</span> Ukrainian physicist

Yuriy Reznikov was a Ukrainian physicist, Head of the Department of Crystals at NASU Institute of Physics and a world-renown expert in the field of liquid crystals. He is known for his work on photoalignment, "giant" optical non-linearity of liquid crystals and nano-colloids.

References

  1. 1 2 3 4 5 Zannoni, Claudio (2022). Liquid crystals and their computer simulations. Cambridge, United Kingdom: Cambridge University Press. p. 15. ISBN   978-1-108-53963-0.
  2. Gray, George William; Harrison, Ken J.; Nash, J A. (1973). "New family of nematic liquid crystals for displays". Electronics Letters. 9 (6): 130–131. Bibcode:1973ElL.....9..130G. doi:10.1049/el:19730096.
  3. 1 2 Collings, Peter J.; Hird, Michael (1997). Gray, George William; Goodby, J. W.; Fukuda, A. (eds.). Introduction to Liquid Crystals: Chemistry and Physics . Taylor and Francis Ltd. pp. 53, 151–152. ISBN   0-7484-0643-3.

Further reading