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1.
Chem Commun (Camb) ; 55(34): 4961-4964, 2019 Apr 23.
Article in English | MEDLINE | ID: mdl-30963148

ABSTRACT

A molecular three-input AND logic gate with a naphthalimide fluorophore communicates the presence of a congregation of three biologically relevant cations in aqueous methanol with a 25-fold fluorescence enhancement and ΦFmax of 0.203.

2.
Org Biomol Chem ; 15(47): 10116-10121, 2017 Dec 06.
Article in English | MEDLINE | ID: mdl-29170771

ABSTRACT

A novel fluorescent molecular logic gate with a 'fluorophore-spacer1-receptor1-spacer2-receptor2' format is demonstrated in 1 : 1 (v/v) methanol/water. The molecule consists of an anthracene fluorophore, and tertiary alkyl amine and N-(2-methoxyphenyl)aza-15-crown-5 ether receptors. In the presence of threshold concentrations of H+ and Na+, the molecule switches 'on' as an AND logic gate with a fluorescence quantum yield of 0.21 with proton and sodium binding constants of log ßH+ = 9.0 and log ßNa+ = 3.2, respectively. At higher proton levels, protonation also occurs at the anilinic nitrogen atom ether with a log ßH+ = 4.2, which allows for Na+, H+-enabled OR (OR + AND circuit) and H+-driven ternary logic functions. The reported molecule is compared and contrasted to classic anthracene-based Na+ and H+ logic gates. We propose that such logic-based molecules could be useful tools for probing the vicinity of Na+, H+ antiporters in biological systems.


Subject(s)
Amines/chemistry , Anthracenes/chemistry , Crown Ethers/chemistry , Fluorescent Dyes/chemistry , Hydrogen/chemistry , Sodium/chemistry , Fluorescent Dyes/chemical synthesis , Methanol/chemistry , Molecular Structure , Water/chemistry
3.
Beilstein J Org Chem ; 12: 1503-11, 2016.
Article in English | MEDLINE | ID: mdl-27559403

ABSTRACT

The flow synthesis of ortho-substituted carboxylic acids, using carbon monoxide gas, has been studied for a number of substrates. The optimised conditions make use of a simple catalyst system compromising of triphenylphosphine as the ligand and palladium acetate as the pre-catalyst. Carbon monoxide was introduced via a reverse "tube-in-tube" flow reactor at elevated pressures to give yields of carboxylated products that are much higher than those obtained under normal batch conditions.

4.
Beilstein J Org Chem ; 12: 1598-607, 2016.
Article in English | MEDLINE | ID: mdl-27559412

ABSTRACT

A flow system to perform Chan-Lam coupling reactions of various amines and arylboronic acids has been realised employing molecular oxygen as an oxidant for the re-oxidation of the copper catalyst enabling a catalytic process. A tube-in-tube gas reactor has been used to simplify the delivery of the oxygen accelerating the optimisation phase and allowing easy access to elevated pressures. A small exemplification library of heteroaromatic products has been prepared and the process has been shown to be robust over extended reaction times.

5.
Beilstein J Org Chem ; 11: 875-83, 2015.
Article in English | MEDLINE | ID: mdl-26124889

ABSTRACT

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.

6.
Chem Commun (Camb) ; 50(8): 1009-11, 2014 Jan 28.
Article in English | MEDLINE | ID: mdl-24310372

ABSTRACT

A novel supramolecular three-input AND logic gate is demonstrated as a 'lab-on-a-molecule' for monitoring the Na(+), pH and pE levels in solution by communicating a fluorescence signal. The fluorescence signal is modulated by three photoinduced electron transfer reactions that are controlled by an unprecedented combination of two cation binding events and one redox reaction.

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