Synthesis, Optoelectronic, and Photoelectrochemical Properties of an Azulene-Bridged Porphyrin Dimer

Document Type

Article

Publication Title

ACS Omega

Abstract

Although azulene-incorporated porphyrin analogues, referred to as ″azuliporphyrins”, are well documented in the literature, the studies available on covalently tethered azulene–porphyrin hybrid molecules are limited. This work reports the synthesis of 1,3-azulene-bridged porphyrin dimers 3 and 4, achieved through the Suzuki–Miyaura cross-coupling reaction. The optoelectronic properties, photophysical behavior, excited-state dynamics, and potential application of dimer 4 in photoelectrochemical water splitting (PEC-WS) are investigated. Dimer 4 exhibits a smaller HOMO–LUMO gap and a lower ionization potential than the corresponding monomer 5. However, despite having an extended π-conjugation, the V-shaped geometry of the dimer restricts its long-range aggregation and charge/exciton delocalization in comparison to its corresponding monomer. The computational electronic structure analysis complements the experimental findings. The results presented in this paper provide rational insights into the structure–property correlation within the less explored azulene–porphyrin hybrid systems.

First Page

52473

Last Page

52482

DOI

10.1021/acsomega.5c05525

Publication Date

11-11-2025

This document is currently not available here.

Share

COinS