3,4,9,10‐Perylenetetracarboxylic Acid Derivatives, Their Spectral Behavior and Their Chemical Interaction with Hydrated Iron Oxide Nanopar

Abstract

The photophysical properties such as electronic absorption, excitation and emission spectra as well as molar absorptivity and fluorescence quantum yield of N, 4,9, N,4,9, and N,N-bis(4-methylpyridenyl)-3,4,9,10-perylenetetracarboxylic diimide (MPyPBD) have been measured in different solvents. Both electronic absorption and fluorescence spectra are not sensitive to medium polarity, while the fluorescence quantum yield (φ f ) is solvent dependent. Perylene derivatives under investigation undergo molecular aggregation to dimmer or larger aggregates in water. Dye solution in dimethylformmaide (DMF) gives laser emission at 565 nm upon pumping with 337.1 nm nitrogen laser pulse. The excitation energy transfer from 7-dimethylamino-4-methylcoumarine (DMC) to PmPBD has been studied to improve the laser emission of PmPBD. The value of energy transfer rate constant (k ET ) and critical transfer distance (R 0 ) indicate a Förster type energy transfer mechanism. There is a large interaction between the perylene compounds under investigation and the hydrated nanoparticles in the excited state therefore the fluorescence quenching rate constant of these derivatives by hydrated iron oxide nanoparticles has a large value.

Spectral characteristics and fluorescence quenching of N,N′-bis(4-pyridyl)-3,4:9,10-perylenebis(dicarboximide) (BPPD)

“…The loss of vibrational structure in the emission spectrum of BPPD in polar protic solvents was attributed to the interaction between hetero-atoms of BPPD molecule and the alcohol, which occurred during the lifetime of excited singlet state. A similar behavior has been reported earlier for some perylene derivatives [41]. The spectral data of BPPD in different solvents are listed in Table 1.…”

Singlet oxygen production by a polypyridine ruthenium (II) complex with a perylene monoimide derivative: A strategy for photodynamic inactivation of Candida albicans

“…This might include generation of singlet oxygen, and subsequent pollutant degradation and photodynamic activity [7,10,15]. A number of perylene-3,4,9,10-tetracarboxylic acid (diimide) derivatives, known as PDIs, and polypyridine complexes derived from perylenes have shown good results in the production of reactive species of reactive oxygen species (ROS) [11,[16][17][18]. The ligands containing the perylene moiety are reddish dyes with very high quantum yields of luminescence.…”

“…The perylene dyes are known for their poor solubility in organic solvents (typically 1-2 mg L À1 ) [11,21,22]. Their PDI diimide derivatives with symmetrical and unsymmetrical secondary, or tertiary alkyl side chains N,N'-bis(1-isobutyl-3 methylbutyl) perylene-3,4:9,10-bis(dicarboximide), N,N'-bis(1-butylhexyl)perylene-3,4:9,10-bis(dicarboximide) and N,N'-bis(5-tert-butyl-1,3,4-thiadiazole-2-yl)perylene-3,4:9, 10-bis(dicarboximide) were synthesized and had significantly improved solubility (10 mg/mL) in dichloromethane, chloroform, ether, hexane, chlorobenzene and toluene [16,17]. Single or double amine substitution on the perylene core can also lead to a red shift of the absorption maximum up to 750 nm [11,22,23].…”

“…The approximate mirror-image relation between the absorption and fluorescence bands at 460 nm and 490 nm are caused by relatively small differences between the geometry of the ground S 0 and excited singlet state S 1 , which are typical for the rigidity and planarity of the polycyclic aromatic molecules [17,22,42].…”

“…The ability to produce singlet oxygen depends largely on the production of a long-lived triplet state, [13,14,17,18] and the moderate quantum yield values of 1 O 2 and the high absorbance of the perylene moiety in the visible range make cis-[Ru (phen) 2 (pPDI)] 2+ a possible photosensitizer to be used in water disinfection or other singlet oxygen-base processes that use sunlight as an excitation source. Since the Ru complex has a long-lived triplet state, it is of possible that in addition to formation of singlet oxygen, formation of superoxide anion by electrontransfer processes and/or Type I photooxidation processes take place upon irradiation of the Ru complex under aerobic conditions.…”