Related Experiment Video
Updated: May 26, 2026
08:51
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
5,8-Dibromo-15-cyano-2,11-dithia-[3.3]paracyclo-phane
1Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Acta Crystallographica. Section E, Structure Reports Online
|December 27, 2011
Summary
This study investigates the crystal structure of a novel dibromo-dithia-tricyclo-octadecene derivative. Results reveal strong π-π interactions due to close aromatic ring packing, with disordered sulfur atoms.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Understanding molecular packing is crucial for predicting material properties.
- π-π interactions significantly influence the solid-state behavior of organic molecules.
- Novel polycyclic compounds with heteroatoms offer unique structural motifs.
Purpose of the Study:
- To elucidate the crystal structure of 13,15-dibromo-3,10-dithia-tricyclo-[10.2.2.2(5,8)]octa-deca-1(14),5,7,12,15,17-hexa-ene-6-carbonitrile.
- To analyze the intermolecular interactions, particularly π-π stacking, within the crystal lattice.
- To investigate the presence and nature of disorder in the molecular structure.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
- Analysis of bond lengths, bond angles, and dihedral angles provided insights into molecular geometry.
- Intermolecular distances and packing arrangements were examined to quantify π-π interactions.
Main Results:
- The crystal structure revealed near-parallel benzene rings with a dihedral angle of 1.1(2)°.
- A short centroid-to-centroid distance of 3.294(3) Å between aromatic rings indicates strong π-π interactions.
- One sulfur atom in a bridging chain exhibited positional disorder, distributed over two sites with distinct occupancies.
Conclusions:
- The studied compound exhibits significant π-π interactions, suggesting potential applications in organic electronics or materials science.
- The observed disorder in the sulfur atom highlights the complex packing arrangements possible in such polycyclic systems.
- Further studies could explore the impact of this structural arrangement on the compound's physical and chemical properties.
More Related Videos
Related Concept Videos
01:18Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Removing one hydrogen from the intervening CH2 group with both...
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
02:37Disubstituted Cyclohexanes: cis-trans Isomerism
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
01:13Five-Membered Heterocyclic Aromatic Compounds: Overview
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
02:46Halogenation of Alkenes
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
01:14Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.