Impact of Heterocycle Annulation on NIR Absorbance in Quinoid Thioacene Derivatives.
Peng HouSebastian PeschtrichNils HuberWolfram FeuersteinAngela BihlmeierIvo KrummenacherRoland SchochWillem KlopperFrank BreherJan ParadiesPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2022)
The synthesis and characterisation of a homologous series of quinoid sulfur-containing imidazolyl-substituted heteroacenes is described. The optoelectronic and magnetic properties were investigated by UV/vis, fluorescence and EPR spectroscopy as well as quantum-chemical calculations, and were compared to those of the corresponding benzo congener. The room-temperature and atmospherically stable quinoids display strong absorption in the NIR region between 678 and 819 nm. The dithieno[3,2-b:2',3'-d]thiophene and the thieno[2',3':4,5]thieno[3,2-b]thieno[2,3-d]thiophene derivatives were EPR active at room temperature. For the latter, variable-temperature EPR spectroscopy revealed the presence of a thermally accessible triplet state, with a singlet-triplet separation of 14.1 kJ mol -1 .
Keyphrases
- room temperature
- energy transfer
- photodynamic therapy
- single molecule
- high resolution
- ionic liquid
- molecular dynamics
- quantum dots
- fluorescence imaging
- drug release
- fluorescent probe
- atomic force microscopy
- solid state
- dna repair
- molecular dynamics simulations
- dna damage
- structure activity relationship
- density functional theory
- molecular docking
- single cell
- light emitting
- liquid chromatography
- monte carlo
- drug delivery