Synthesis and properties of β-arylated triphyrins[2.1.1] by successive introduction of one to six aryl groups at the β-pyrrole carbons
Year: 2024
Type: article
Abstract: A series of β-arylated meso-tetra(p-tolyl) triphyrins[2.1.1] by successively increasing the number of p-fluorophenyl groups from one to six at the β-pyrrole carbons were synthesized by reacting appropriate β-bromo triphyrin[2.1.1] with p-fluorophenyl boronic acid in toluene/THF/H2O (1:1:1) at 80 οC for 4 h - 24 h. The increase of the number of p-fluorophenyl groups at the β-pyrrole carbons induces steric hindrance at the periphery of triphyrin[2.1.1] that results in the alteration of electronic properties due to distortion in the macrocycle which is reflected in their structure, spectral and redox properties. The X-ray structure analysis revealed that β-di(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1] was almost planar like meso-tetra(phenyl) triphyrin[2.1.1] whereas the β-hexa(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1] was significantly distorted. The absorption spectra of β-arylated triphyrins[2.1.1] showed bathochromically shifted Soret and Q-bands with reduction in absorption coefficients and increase in the bandwidth compared to the β-unsubstituted meso-tetra(p-tolyl) triphyrin[2.1.1] and the maximum effects were noted for β-hexa(p-fluorophenyl) meso-tetra(p-tolyl) triphyrin[2.1.1]. The β-arylated meso-tetra(p-tolyl) triphyrins[2.1.1] are stable under electrochemical conditions and DFT/TD-DFT studies are in agreement with the experimental observations.
Source: Tetrahedron
Authors: Akrti Sharma, Mangalampalli Ravikanth
Institution: Indian Institute of Technology Bombay
Language: English
Subfield: Materials Chemistry
Field: Materials Science
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,500
OpenAlex ID: W4403936564