188-52-3

Basic information

• Product Name: (5)HELICENE
• Synonyms: (5)HELICENE;DIBENZO(C,G)PHENANTHRENE;[pR,(-)]-Dibenzo[c,g]phenanthrene;(+)-Pentahelicene;[pS,(+)]-Dibenzo[c,g]phenanthrene
• CAS NO: 188-52-3
• Molecular Formula: C₂₂H₁₄
• Molecular Weight: 278.35
• Mol File: 188-52-3.mol
• Article Data: 21

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 524.7°Cat760mmHg
• Flash Point: 264.5°C
• Appearance: /
• Density: 1.232g/cm³
• Vapor Pressure: 1.41E-10mmHg at 25°C
• Refractive Index: 1.811
• CAS DataBase Reference: (5)HELICENE(CAS DataBase Reference)
• NIST Chemistry Reference: (5)HELICENE(188-52-3)
• EPA Substance Registry System: (5)HELICENE(188-52-3)

Safety Data

• Hazardous Substances Data: 188-52-3(Hazardous Substances Data)

Usage

Description

(5)HELICENE is a class of organic compounds characterized by their helical (spiral) molecular structure, consisting of a series of linked benzene rings twisted around a central axis. This unique structure has garnered significant interest in organic chemistry and materials science due to their potential applications and properties such as chirality and helicity.

Uses

Used in Molecular Electronics:
(5)HELICENE is used as a component in molecular electronics for its unique helical structure and electronic properties, which can contribute to the development of new functional materials and chemical processes.
Used in Chiral Catalysis:
(5)HELICENE is used as a chiral catalyst to facilitate asymmetric reactions, taking advantage of its chirality to induce selectivity in chemical transformations.
Used in Optoelectronics:
(5)HELICENE is used as a material in optoelectronic devices due to its potential to manipulate light and its electronic properties, which can be harnessed for applications such as organic light-emitting diodes (OLEDs).
Used in Liquid Crystals:
(5)HELICENE is used as a chiral dopant in liquid crystals, where its helicity can influence the alignment and properties of the liquid crystal medium.
Used in Fluorescent Materials:
(5)HELICENE is used as a fluorescent material in organic light-emitting diodes (OLEDs), leveraging its optical properties to enhance the performance of these devices.

InChI:InChI=1/C22H14/c1-3-7-19-15(5-1)9-11-17-13-14-18-12-10-16-6-2-4-8-20(16)22(18)21(17)19/h1-14H

Upstream product

• 457885-21-1 bis[2-((1Z)-1-buten-3-ynyl)phenyl]acetylene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 2633-08-1 cis-1,2-bis(2-naphthyl)ethylene 
• 1250981-24-8 5,6,9,10-tetrahydropentahelicene-5,10-diyl diacetate 
• 139371-87-2 2-Bromo-1,4-bis-[(Z)-2-(4-bromo-phenyl)-vinyl]-benzene 
• 602-09-5 1,1'-bi-2-naphthol 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 117582-62-4 1-bromo-2-formyl-3,4-dihydronaphthalene 
• 103989-84-0 2-methyl-1-naphthylboronic acid 
• 2586-62-1 1-bromo-2-methylnaphtalene 
• 827346-97-4 1-(2-methyl-1-naphthyl)-3,4-dihydronaphthalene-2-carbaldehyde 
• 796843-13-5 2-ethynyl-1,1’-binaphthalene 
• 118-92-3 anthranilic acid 
• 211235-96-0 1,2-dihydro-3-vinyl-phenanthrene 

Downstream Products

• 191-24-2 Benzo[ghi]perylene 

Relevant articles and documents

Coordination chemistry of cyclopropenylidene-stabilized phosphenium cations: Synthesis and reactivity of Pd and Pt complexes

A straightforward synthesis of cyclopropenylidene-stabilized phosphenium cations 1 a-g through the reaction of [(iPr2N)2C 3+Cl]BF4 with secondary phosphines is described. Their donor ability was evalu

Toward a visible light mediated photocyclization: Cu-based sensitizers for the synthesis of [5]helicene

A photochemical synthesis of [5]helicene employing a copper-based sensitizer 7 has been developed that avoids the disadvantages associated with the traditional UV light mediated method. The visible light mediated synthesis uses common glassware and a simple household light bulb without the competing formation of [2 + 2] cycloadducts, regioisomers, or the overoxidation product benzo[ghi]perylene 3. Preliminary results show that the reaction time can be significantly reduced through the use of a continuous flow strategy.

Helicene synthesis by Br?nsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]

A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C-C bond formation by Suzuki-Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.

Facile photochemical synthesis of 5,10-disubstituted [5]helicenes by removing molecular orbital degeneracy

Photocyclodehydrogenation is a key reaction to synthesize helicenes; however, because of overannulation, it is not applicable to the synthesis of [5]helicene. Introduction of a cyano group was found to remove the orbital degeneracy of the low-lying unoccupied MOs; consequently, the lowest excitation comprises a single transition involving the C2-antisymmetric MO. Therefore, the problematic overannulation can be effectively suppressed. Moreover, in combination with the Knoevenagel reaction, a one-pot synthesis of 5,10-dicyano[5]helicene with 67% yield was accomplished.