Related Experiment Video
Updated: Oct 14, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Inverted and fused expanded heteroporphyrins.
Rima Sengupta1, Mangalampalli Ravikanth1, Tavarekere K Chandrashekar2
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. ravikanth@chem.iitb.ac.in.
This review explores inverted and fused expanded heteroporphyrins, large macrocycles with unique structural and electronic properties due to inverted heterocyclic rings. These compounds offer novel characteristics for advanced material applications.
Area of Science:
- * Organic Chemistry
- * Supramolecular Chemistry
- * Materials Science
Background:
- * Expanded heteroporphyrins are large macrocycles (>17 atoms, >18 π electrons) comprising diverse heterocyclic rings.
- * These macrocycles exhibit structural flexibility, often adopting inverted conformations of pyrrole/heterocycle units.
- * Inverted conformations lead to two classes: N-inverted and hetero-atom inverted expanded heteroporphyrins.
Purpose of the Study:
- * To review the synthesis, structure, and properties of inverted and fused expanded heteroporphyrins.
- * To highlight the unique features arising from inverted and fused structures.
- * To cover compounds with varying numbers of heterocyclic rings (5 to 8+).
Main Methods:
- * Literature review focusing on synthesis strategies.
- * Structural analysis of inverted and fused macrocycles.
- * Examination of aromaticity, electronic, and coordination properties.
Main Results:
- * Inverted expanded heteroporphyrins display distinct structural, aromatic, electronic, and coordination behaviors.
- * Fused expanded heteroporphyrins, formed via intramolecular fusion, possess unique characteristics compared to their non-fused counterparts.
- * The study encompasses a range of expanded heteroporphyrins, from pentaphyrins to larger systems.
Conclusions:
- * Inverted and fused expanded heteroporphyrins represent a significant class of macrocyclic compounds with tunable properties.
- * Their unique conformations and electronic structures offer potential for novel applications.
- * Further research into their synthesis and properties will drive advancements in chemical and material sciences.
Related Concept Videos
Five-Membered Heterocyclic Aromatic Compounds: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
Hybridization of Atomic Orbitals II
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
