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Related Concept Videos

IR Absorption Frequency: Hybridization01:21

IR Absorption Frequency: Hybridization

636
Hydrocarbons such as alkanes, alkenes, and alkynes show characteristic C–H stretching absorption bands. These IR stretching frequencies depend on the hybridization of the involved carbon atom and can be explained in terms of the s character of each hybridized atomic orbital.
Among the sp, sp2, and sp3 hybridized orbitals, sp orbitals have the maximum s character (50%). Consequently, the electrons are held more closely to the nucleus, resulting in stronger and shorter C–H bonds that...
636
UV–Vis Spectroscopy of Conjugated Systems01:32

UV–Vis Spectroscopy of Conjugated Systems

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Organic compounds with conjugated double bonds show strong absorption features in the UV–visible region of the electromagnetic spectrum attributed to π → π* electronic excitations. Generally, a UV–vis absorption spectrum is recorded as a plot of absorbance vs wavelength. The wavelength of maximum absorbance, which manifests as a peak in the absorption spectrum, is denoted as λmax.
One of the factors influencing λmax is the extent...
6.9K
IR Absorption Frequency: Delocalization01:04

IR Absorption Frequency: Delocalization

733
Electron delocalization refers to the distribution of electrons across multiple atoms within a molecule rather than being confined to a single atom or bond. This phenomenon is common in systems with conjugated bonds—structures where alternating single and double bonds allow π-electrons to move freely across the network. The movement of electrons stabilizes the molecule and can affect various chemical properties, including vibrational frequencies observed in IR spectroscopy.
In IR...
733
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.8K
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...
2.8K

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Related Experiment Video

Updated: Jun 10, 2025

Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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Azatriangulene-Based Conductive C═C Linked Covalent Organic Frameworks with Near-Infrared Emission.

Ehsan Hamzehpoor1, Pegah Ghamari1, Yuze Tao1

  • 1Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, H3A 09B, Canada.

Advanced Materials (Deerfield Beach, Fla.)
|October 21, 2024
PubMed
Summary

New covalent organic frameworks (COFs) exhibit near-infrared emission and high electrical conductivity. These materials show potential for humidity sensing and advanced electronic applications due to their tunable properties.

Keywords:
covalent organic frameworks (COF)near‐infrared luminescencesemiconducting COFtrioxaazatriangulene

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent Organic Frameworks (COFs) are crystalline porous polymers with tunable electronic and optical properties.
  • Developing NIR-emissive COFs is crucial for applications in sensing and optoelectronics.
  • Understanding structure-property relationships in COFs is key to optimizing their performance.

Purpose of the Study:

  • Synthesize and characterize novel NIR-emissive π-conjugated COFs.
  • Investigate the impact of linker rigidity on electronic and optical properties.
  • Explore potential applications in humidity sensing and electrical conductivity.

Main Methods:

  • Knoevenagel condensation for COF synthesis.
  • Spectroscopic techniques (UV-Vis, fluorescence) for optical characterization.
  • Electrical conductivity measurements and DFT calculations for electronic properties.

Main Results:

  • Two NIR-emissive COFs, pTANG1 and pTANG2, were successfully synthesized.
  • pTANG1 demonstrated significant NIR emission (λmax = 789 nm) and humidity-sensitive fluorescence quenching.
  • p-Doping dramatically enhanced electrical conductivity, reaching 0.65 S cm⁻¹ for pTANG1, the highest for C═C linked COFs.

Conclusions:

  • The rigidity of the phenylene linker in pTANG1 enhances conjugation, leading to superior NIR emission and electrical conductivity compared to pTANG2.
  • These COFs show promise as efficient humidity sensors and highly conductive materials for electronic devices.