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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,...
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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.
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Photoactive Thiophene-Enriched Tetrathienonaphthalene-Based Covalent Organic Frameworks.

Tianhao Xue1, Marcello Righetto2, Roman Guntermann1

  • 1Department of Chemistry and Center for NanoScience (CeNS), Ludwig-Maximilians-Universität (LMU), Butenandtstraße 5-13, 81377, Munich, Germany.

Small (Weinheim an Der Bergstrasse, Germany)
|November 7, 2025
PubMed
Summary
This summary is machine-generated.

Novel thiophene-enriched covalent organic frameworks (COFs) were synthesized using a tetrathienonaphthalene (TTNTA) node. These COFs exhibit excellent optoelectronic properties and photoactivity, showing potential for applications in solar energy conversion and optoelectronics.

Keywords:
covalent organic frameworksoptical‐pump terahertz‐probe spectroscopyphotoactivetetrathienonaphthalene

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent Organic Frameworks (COFs) offer tunable optoelectronic properties through molecular design.
  • Thiophene-based materials are crucial for enhancing charge transport in organic electronics.

Purpose of the Study:

  • To synthesize novel thiophene-enriched COFs using a tetrathienonaphthalene (TTNTA) building block.
  • To investigate the optoelectronic properties and photoactivity of these new COFs for potential applications.

Main Methods:

  • Facile synthesis of TTNTA node and subsequent construction of imine-linked COFs (TT COF and BDT(BT)2 COF) using aldehyde-functionalized linkers.
  • Solvothermal method for preparing highly crystalline and oriented COF films.
  • Optical-pump terahertz-probe spectroscopy for charge-carrier mobility measurements.
  • Photoelectrochemical water splitting experiments to assess photoactivity.

Main Results:

  • High crystallinity and orientation achieved for TTNTA-based COF films.
  • Effective charge-carrier mobilities of 0.34 ± 0.04 cm²V⁻¹s⁻¹ (TT COF) and 0.18 ± 0.02 cm²V⁻¹s⁻¹ (BDT(BT)2 COF) were measured.
  • Demonstrated photoactivity as photocathodes in water splitting, yielding photocurrent densities of 10 and 15.3 µA cm⁻².

Conclusions:

  • TTNTA-based COFs possess significant potential for optoelectronic applications.
  • The design of thiophene-enriched COFs with high crystallinity and photoactivity is feasible.
  • These materials show promise for efficient solar energy conversion technologies.