Pyrene Appended Free‐base, Phosphorus(V) and Gallium(III) Corroles and Their β,β′‐Linked Corrole Dimers: Synthesis, Photophysical and Electrochemical Properties

Abstract

Pyrene appended free‐base, phosphorus(V) and gallium (III) corrole conjugates were synthesized and characterized. Efficient β‐β′ dimerization of corroles was achieved by oxidation with p‐chloranil in moderate yield from their respective metallated corroles. The weak ground state electronic coupling between pyrene and corrole units was established by photophysical and electrochemical investigations. The fluorescence spectral studies showed a red shifted emission maximum for dimer with respect to their monomeric counterpart due to possible π‐conjugation and supported by the density functional theory (DFT). The electrochemical investigation revealed multiple oxidation associated with the corrole and pyrene centers.

Can Corrole Dimers Be Good Photosensitizers to Kill Bacteria?

“…The electronic absorption spectra of the synthesized gallium(III) corrole dimers were recorded in DMF (Figure 1). The UV-vis spectra of corrole dimers 3 and 4 revealed the characteristic profile of corrole derivatives, dominated by a Soret-type band at 426 and 425 nm, respectively, and weak and broader Q bands ranging from 550-670 nm [41]. Notice that the Q-band for the corrole dimers 3 and 4 exhibited a red-shift when compared to the corrole precursor 1.…”

“…425 nm, respectively, and weak and broader Q bands ranging from 550-670 nm [41]. Notice that the Q-band for the corrole dimers 3 and 4 exhibited a red-shift when compared to the corrole precursor 1.…”

Excitation wavelength-reliant light-induced energy and electron processes in pyrene and naphthalene functionalized dual-dye integrated polyaromatic azaborondipyrromethenes

“…Several lab-made artificial photosynthetic systems comprising naphthyl or pyrenyl moieties covalently tethered to photo- and electro-active entities such as ferrocene, 23–29 porphyrin, 14,30–41 corrole, 16,42–45 perylene, 46–50 borondipyrromethenes (BODIPYs), 51–60 azaBODIPYs, 8,17,61,62 and C 60 63–65 have been synthesized and effectively utilized as light harvesting molecules, 8,14,16,17,34,36,38,47,48,54–56,62,63,66–71 light capturers in dye sensitized solar cells (DSSCs) 30,35,37,40,41,72 and organic solar cells, 46,60,64,65 catalysts in H 2 and O 2 evolution, 44,45 photocatalysts, 32,73 molecular sensors, 23–26,52 sensitizers in photodynamic therapy and singlet oxygen generation, 31,33,59,61 DNA binders, 42 and biological imaging agents, 57 and also for photo-upconversion. 74…”

“…4 In addition to attractive photophysical properties, it bears high chemical stability and charge-carrier mobility; making it an active ingredient of organic light emitting diodes, 18 organic field effect transistors, 19 organic photovoltaics, 4 and sensors. [20][21][22] Several lab-made artificial photosynthetic systems comprising naphthyl or pyrenyl moieties covalently tethered to photoand electro-active entities such as ferrocene, [23][24][25][26][27][28][29] porphyrin, 14,[30][31][32][33][34][35][36][37][38][39][40][41] corrole, 16,[42][43][44][45] perylene, [46][47][48][49][50] borondipyrromethenes (BODIPYs), [51][52][53][54][55][56][57][58][59][60] azaBODIPYs, …”