Tools
ToolsAlanazi, Budur N., Alsahli, Ahad O., Remiro-Buenamañana, Sonia, Díaz-Moscoso, Alejandro, Alkorbi, Faeza H., Alsaiari, Norah A., Marrett-Munro, Conor, Chambrier, Isabelle, Hughes, David L., Coles, Simon J., Tizzard, Graham J. and Cammidge, Andrew Neil (2025) A family of symmetrical and unsymmetrical aza-dipyrromethenes and aza-BODIPYs with through-bond and face-to-face p‐-interaction between termini. Chemistry – A European Journal, 31 (50). ISSN 0947-6539
Preview |
PDF (Alanazi_etal_2025_ChemistryAEuropeanJ)
- Published Version
Available under License Creative Commons Attribution. Download (1MB) | Preview |
Abstract
The dipyrromethenes (DPMs) and their borylated adducts (BODIPYs) constitute a class of versatile chromophores that has become one of the most widely studied over recent decades. They combine excellent photochemistry properties with opportunity for synthetic manipulation and tuning. We report here a related class of aza-dibenzodipyrromethenes and show that they present an interesting architecture where the core adopts a helical arrangement that places terminal aryl functional groups directly on top of each other in close, π-stacked arrangement. Complexation by reaction with boron trifluoride, demonstrated to be significantly improved by addition of trimethylsilyl chloride, induces a stereochemical inversion that destroys the helix, flattens the system, and switches on fluorescence. A wide range of terminal aromatic fragments can be easily introduced. Unsymmetrical derivatives can be made conveniently by simple mixed condensations, but a controlled, rational approach is also described whereby the ability of one component to homocondense (the more reactive partner) is removed by conversion to its corresponding tosylate or triflate. The two approaches have been investigated through successful introduction of complementary electron rich, electron poor, and π-extended functional termini.
| Item Type: | Article |
|---|---|
| Additional Information: | Data Availability Statement: The data that support the findings of this study are available from the corresponding author upon reasonable request. Funding information: EPSRC (SJC and GJT at Southampton, plus grant EP/S005854/1 at UEA), the Ministry of Education, Saudi Arabia (AOA) and Saudi Cultural Bureau, Princess Nourah Bint Abdul Rahman university (BNA), Najran university (FHA, NAA). |
| Uncontrolled Keywords: | bodipy,chromophores,helicene,switching,synthesis,chemistry(all),catalysis,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology Faculty of Science > School of Chemistry (former - to 2024) Faculty of Science |
| UEA Research Groups: | Faculty of Science > Research Groups > Centre for Photonics and Quantum Science Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Chemistry of Light and Energy |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 11 Jul 2025 16:30 |
| Last Modified: | 08 Sep 2025 15:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/99894 |
| DOI: | 10.1002/chem.202501862 |
Downloads
Downloads per month over past year
Actions (login required)
 |
View Item |