Browsing Thompson, Alison by Title
Now showing items 17-36 of 58
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Facile Deprotection of F-BODIPYs using Methylboronic Acid
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) are deprotected through removal of the –BF2 moiety upon treatment with methylboronic acid. The tolerance of various substitution patterns about the dipyrrinato core ... -
The first series of alkali dipyrrinato complexes
The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, ... -
Heteroleptic zinc dipyrromethene complexes
H-1 NMR spectroscopy has been used to study the complexation of a per-alkyl dipyrromethene with zinc acetate. An intermediate, assigned to be the heteroleptic Zn(dipyrromethene) (acetate) complex, is observed under titration ... -
An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s
An improved methodology for the synthesis of F-BODIPYs from dipyrrins and bis(dipyrrin)s is reported. This strategy employs lithium salts of dipyrrins as intermediates that are then treated with only one equivalent of boron ... -
Influence of B-Ring Modifications on Proton Affinity, Transmembrane Anion Transport and Anti-Cancer Properties of Synthetic Prodigiosenes
Prodigiosin is the parent compound of the tripyrrolic natural products known as the prodigiosenes. Some of these natural products and their synthetic analogs show anti-cancer, immunosuppressive and antimicrobial actions, ... -
Investigations into the nucleophilic meso-substitution of F-BODIPYs and improvements to the synthesis of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene.
A series of three F-BODIPYs, with varying levels of steric crowding about the meso-position were selected to investigate nucleophilic meso-substitution of F-BODIPYs. The synthesis of one of these F-BODIPYs, 4,4-difluor ... -
Investigations regarding the utility of prodigiosenes to treat leukemia
Prodigiosenes, possessing a 4-methoxypyrrolyldipyrrin skeleton, are known for their anti-cancer activity. Structural modification of the C-ring resulted in a series of prodigiosenes that displayed promising activity against ... -
Isolation and characterization of a novel tetrahydro-[2,2 ']bipyrrolyl dimer as an impurity from a Knorr reaction
A novel dimer, tetraethyl 2,2',3,3'-tetramethyl-1,1',2,2'-tetrahydro-4H,4'H-2,2'-bipyrrolyi-5,5,5',5'-tetracarboxylate, has been isolated as an impurity (0.4% yield) from a Knorr reaction for the synthesis of ... -
Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate
Benzyl 3,5-dimethyl-pyrrole-2-carboxylate, a very useful pyrrole in porphyrin and dipyrromethene synthesis, can be synthesized via the Knorr-type reaction, but in low yield. Alternative routes to benzyl 3,5-dimethyl-pyrr ... -
Microwave-assisted reduction of F-BODIPYs and dipyrrins to generate dipyrromethanes
The reduction of BODIPYs and dipyrrins to dipyrromethanes, via a reaction involving ethylene glycol and sodium methoxide, is reported. When benzyl alcohol is used in place of ethylene glycol, the addition of 2,4-dinitrop ... -
Photo-induced Anticancer Activity and Singlet Oxygen Production of Prodigiosenes
The photo-induced cytotoxicity of prodigiosenes is reported. One prodigiosene represents a synthetic analogue of the natural product prodigiosin, and two are conjugated to molecules that target the estrogen receptor (ER). ... -
The Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes
The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular ... -
Regioselective Substituent Effects upon the Synthesis of Dipyrrins from 2-Formyl Pyrroles
The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through the adoption of two mechanistic pathways. The key ... -
Robust Synthesis of F-BODIPYs
F-BODIPYs are widely used in applications that rely upon their highly tunable optical properties. A protocol is established for the high-yielding synthesis of F-BODIPYs involving non-anhydrous reagents and not requiring ...