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  • Characterization of novel perylene diimides containing aromatic amino acid side chains.

Characterization of novel perylene diimides containing aromatic amino acid side chains.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy (2015-08-25)
Mohammed J Farooqi, Mark A Penick, Jessica Burch, George R Negrete, Lorenzo Brancaleon
초록

Perylene diimide derivatives have attracted initial interest as industrial dyes. Recently, much attention has been focused on their strong π-π stacks resulting from the large PDI aromatic core. These PDI stacks have distinct optical properties, and provide informative models that could mimic light-harvesting systems and initial charge transfer typical of photosynthetic systems. The absorption property of PDI derivatives may be tuned from visible to near-infrared region by peripheral substitution. We have studied a new class of PDI derivatives with aryl substituents derived from the side chains of aromatic aminoacids (Tyrosine, Tryptophan and Phenylalanine). We have investigated their absorption and the fluorescence properties in a set of organic solvents and established their different tendencies to aggregate in solution despite their solubility. Most aggregation appears to be unordered. One PDI analogue (the one formed from Tyr) in Methanol, however, appears to form J-type aggregates. Based on our results the compounds appear to be promising for future investigations regarding the interaction of these dyes with biomolecules.

MATERIALS
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Sigma-Aldrich
Pyridine, ReagentPlus®, ≥99%
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Methanol-12C, 99.95 atom % 12C
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Ethyl alcohol, Pure, 200 proof, anhydrous, ≥99.5%
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Methanol solution, NMR reference standard, 4% in methanol-d4 (99.8 atom % D), NMR tube size 3 mm × 8 in.
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Ethyl alcohol, Pure, 190 proof, meets USP testing specifications
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Dimethyl sulfoxide, anhydrous, ≥99.9%
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Pyridine, anhydrous, 99.8%
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Dimethyl sulfoxide, sterile-filtered, BioPerformance Certified, meets EP, USP testing specifications, suitable for hybridoma
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8-Octanoyloxypyrene-1,3,6-trisulfonic acid trisodium salt, suitable for fluorescence, ≥90% (HPCE)
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Ethyl alcohol, Pure, 190 proof, ACS spectrophotometric grade, 95.0%
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Pyridine, ≥99%
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Dimethyl sulfoxide, meets EP testing specifications, meets USP testing specifications
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Dimethyl sulfoxide, Hybri-Max, sterile-filtered, BioReagent, suitable for hybridoma, ≥99.7%
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Dimethyl sulfoxide, PCR Reagent
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Dimethyl sulfoxide, ≥99.5% (GC), suitable for plant cell culture
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Dimethyl sulfoxide, for molecular biology
Supelco
Methanol solution, contains 0.10 % (v/v) formic acid, UHPLC, suitable for mass spectrometry (MS), ≥99.5%
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Dimethyl sulfoxide, BioUltra, for molecular biology, ≥99.5% (GC)
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Ethanol, ACS reagent, prima fine spirit, without additive, F15 o1
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Dimethyl sulfoxide, ReagentPlus®, ≥99.5%
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Dimethyl sulfoxide, puriss. p.a., dried, ≤0.02% water
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Dimethyl sulfoxide, puriss. p.a., ACS reagent, ≥99.9% (GC)
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Ethyl alcohol, Pure 200 proof, for molecular biology
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Pyridine, puriss. p.a., ACS reagent, reag. Ph. Eur., ≥99.5% (GC)
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Ethyl alcohol, Pure, 200 proof, ACS reagent, ≥99.5%
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Ethyl alcohol, Pure, 200 proof
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Pyridine, ReagentPlus®, ≥99%
Sigma-Aldrich
Ethyl alcohol, Pure, 200 proof, meets USP testing specifications
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Pyridine, biotech. grade, ≥99.9%
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Dimethyl sulfoxide, ACS reagent, ≥99.9%