Thompson, Alison: Recent submissions
Now showing items 1-20 of 59
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A mild synthetic route to α-nitroso diaryl pyrroles (Postprint)
A new synthetic method to access α-nitroso pyrroles is presented. This method utilises the nitrosonium salt NOBF4, enabling short reaction times (<10 minutes) and avoiding the harsh acidic conditions usually associated ... -
A series of potent BODIPY photosensitisers featuring tellurophene motifs at boron† (Postprint)
This article describes the synthesis and photophysical properties of a series of BODIPY photosensitisers that feature tellurophene motifs appended at the boron centre. These compounds were obtained via nucleophilic ... -
BODIPYs with Chalcogenophenes at Boron: Synthesis and Properties. Postprint
Reported herein are the synthesis and characterization of BODIPYs bearing heterocycles at boron. To synthesize this series, various chalcogenophenes (furan, thiophene, selenophene, and tellurophene) were lithiated and then ... -
Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds
Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ... -
Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold
The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub- types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl–B–F intermediate, is implicated in the ... -
Bridging and Conformational Control of Porphyrin Units through Non-Traditional Rigid Scaffolds
Connecting two porphyrin units in a rigid linear fashion, without any undesired electron delocalization or communication between the chromophores, remains a synthetic challenge. Herein, a broad library of functionally ... -
Bis[Pyrrolyl Ru(II)] Triads: a New Class of Photosensitizers for Metal-Organic Photodynamic Therapy
A new family of ten dinuclear Ru(II) complexes based on the bis[pyrrolyl Ru(II)] triad scaffold, where two Ru(bpy)2 centers are separated by a variety of organic linkers, was prepared to evaluate the influence of the ... -
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 ... -
Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles
2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesized using a Knorr-type approach ... -
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 ... -
Classifying donor strengths of dipyrrinato/aza-dipyrrinato ligands
A parameter is reported by which to use 13C NMR chemical shifts to measure and predict the donor capabilities of N^N dipyrrinato and aza-dipyrrinato ligands chelating in L^X fashion. The results enable the rationalisation ... -
Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes
Despite the vast literature that describes reacting folic acid with a pharmacophore, this route is ineffective in providing the correct regioisomer of the resulting conjugate. We herein present a step-wise route to the ... -
Synthesis of Prodigiosene-Estrogen Conjugates: optimization of protecting group strategies and anticancer properties
The tripyrrolic prodigiosene skeleton was conjugated to several estrogen ligands. The conjugation was achieved via an ester linker that proved to be unusually sensitive to hydrolysis during synthesis. This work describes ... -
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 ... -
Synthesis of symmetric meso-H dipyrrin hydrobromides from 2-formyl pyrroles
The reaction of 2-formyl pyrroles in acidic methanol gives the corresponding symmetric, meso-H 4,6-dipyrrin hydrobromides. This convenient strategy involves initial deformylation under the acidic conditions, followed by ... -
The Use of Tin (IV) Chloride to Selectively Cleave Benzyl Esters over Benzyl Ethers and Benzyl Amines
Benzyl esters are cleaved upon reaction with SnCl4, resulting in isolation of the corresponding carboxylic acid. Importantly, benzyl ethers, amines and amides do not undergo debenzylation under these conditions, nor do a ... -
Antimicrobial Activity of Non-natural Prodigiosenes
Tripyrrolic prodigiosenes, derivatives of the natural product prodigiosin, have been produced via multi-step synthesis beginning with 2-formyl pyrroles bearing various functionalities at the 4-position. Two tin complexes ... -
Activation and Deprotection of F-BODIPYs using Boron Trihalides
The activation of F-BODIPYs with boron trihalides, followed by treatment with a nuclephile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the–BF2 moiety and thereby ... -
Synthesis and Characterization of Pyrrolyldipyrrin F-BODIPYs
A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the ...