π-conjugated system

https://doi.org/10.1351/goldbook.08786
Molecule or a part of a molecule, of which structure may be represented as a system of alternating single and multiple bonds, in which, eventually, a multiple bond can be replaced by an atom with a pair of non-bonding electrons or an atom carrying a negative charge.
Notes:
  1. Examples of conjugated systems are conjugated polymers and molecule species whose formulas drawn in terms of the valence bond theory are as follows:
  2. Alternating arrangement of the single and multiple bonds allows the delocalization of electrons, which stabilizes conjugated systems. The most effective stabilization show planary cyclic systems with 2n+2 delocalized electrons (where n is integer), so-called aromatic systems. The last two examples above are the species where the pair non-bonding electrons (thiophene) or electrons of negatively charged atom are delocalized together with π-electrons giving an aromatic system.
  3. Due to the delocalization of electrons a formula drawn in terms of the valence bond theory does not fully describe the structure of a conjugated species, which actually is a combination of two or more limiting or intermediate resonance structures that are in a dynamic equilibrium. The molecular orbital theory which directly provides extended molecular orbitals spread over all contributing atoms allows better understanding of the electronic and optical properties of a conjugated system.
Source:
PAC, 2022, 94, 15. (Glossary of terms relating to electronic, photonic and magnetic properties of polymers (IUPAC Recommendations 2021)) on page 21 [Terms] [Paper]