Acid- and hydrogen-bonding-induced switching between 22-π and 18-π electron conjugations in 2-aminothiazolo[4,5-c]porphycenes

Abstract

[4,5-c]porphycenes to the blue due to a contraction of their aromatic system from 22-p to 18-p electrons. Finally, the aromatic shift has been successfully used to measure the pH using 2-aminothiazoloporphycene-labelled gold nanoclusters, paving the way for the use of these compounds as near infrared pH-sensitive probes.

2 + 2 Can Make Nearly a Thousand! Comparison of Di- and Tetra-Meso-Alkyl-Substituted Porphycenes

“…Among these studies, particularly important in terms of possible applications are those devoted to spectral and photophysical properties. , Porphycenes are very promising as sensitizers in photodynamic therapy, the main, but not the only theme of numerous patents. Other areas of possible use of porphycenes based on interaction with light include photoelectrochemical devices, near-IR absorbing and emitting fluorophores, − preparation of new electrochromic, liquid crystalline, and elastomeric materials. However, comparative research on the photophysical properties of different porphycenes has been rather limited.…”

Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes

“…13,14 Various porphycenes with meso-and b-substituents and their metal complexes have been reported to have tunable functionalities, crystallinities and solubilities. [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] However, the main obstacle to the widespread application of porphycenes is the lack of efficient and economical methods for their production. Therefore, porphycene chemistry has advanced more slowly than that of the parent isomer porphyrin.…”

Effect of β-Substitution and β,β′-Fusion on the Formation of Boron Complexes of Porphycenes

“…Nevertheless, porphycenes were found to show unusual coordinating properties, thus modifying their feature, which emerged as a topic of extensive research. In the process of exploring the photophysical and coordination properties of the porphycenes, the substituents were found to be vital, as their position on the periphery, as well as their nature, played a critical role in controlling the properties and more interestingly the core sizes, thus unusually affecting the coordinating properties.…”