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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-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.
Crystal Field Theory - Octahedral Complexes02:58

Crystal Field Theory - Octahedral Complexes

Crystal Field Theory
To explain the observed behavior of transition metal complexes (such as colors), a model involving electrostatic interactions between the electrons from the ligands and the electrons in the unhybridized d orbitals of the central metal atom has been developed. This electrostatic model is crystal field theory (CFT). It helps to understand, interpret, and predict the colors, magnetic behavior, and some structures of coordination compounds of transition metals.
CFT focuses on...
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous overlap of p...
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic 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...
Organic Compounds03:02

Organic Compounds

All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Frost Circles for Different Conjugated Systems01:18

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.

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Updated: May 13, 2026

Microfluidic-based Synthesis of Covalent Organic Frameworks (COFs): A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
08:42

Microfluidic-based Synthesis of Covalent Organic Frameworks (COFs): A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface

Published on: July 10, 2017

Thiophene-based covalent organic frameworks.

Guillaume H V Bertrand1, Vladimir K Michaelis, Ta-Chung Ong

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

Proceedings of the National Academy of Sciences of the United States of America
|March 13, 2013
PubMed
Summary
This summary is machine-generated.

We synthesized covalent organic frameworks (COFs) using thiophene building blocks. These advanced materials show promise for electronic devices, despite challenges with defect-prone monomers during synthesis.

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent organic frameworks (COFs) offer tunable properties for advanced applications.
  • Thiophene-based monomers are explored for novel electronic material development.
  • Reticular synthesis enables the construction of complex, ordered porous materials.

Purpose of the Study:

  • To synthesize and characterize novel covalent organic frameworks (COFs) incorporating thiophene units.
  • To investigate the impact of bent ditopic monomers on COF synthesis and stability.
  • To explore the potential of these COFs in electronic device applications.

Main Methods:

  • Reticular synthesis of thiophene-based COFs.
  • Characterization using standard analytical techniques (e.g., NMR, PXRD, TGA).
  • Investigation of charge transfer complex formation within the COF architecture.

Main Results:

  • Successful synthesis of thiophene-containing COFs via reticular methods.
  • Identification of bent ditopic monomers, like 2,5-thiophenediboronic acid, as defect-prone.
  • Demonstration of an unusual charge transfer complex formation within the COF structure.
  • Characterization of a novel complex between thieno[3,2-b]thiophene-2,5-diboronic acid and tetracyanoquinodimethane.

Conclusions:

  • Thiophene-based COFs are synthetically accessible through reticular chemistry.
  • Synthetic control over defect-prone monomers is crucial for COF quality.
  • The unique architecture of these COFs facilitates charge transfer complex formation, advancing their potential for electronic applications.