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Mechanosynthesis of Polyureas and Studies of Their Responses to Anions.

ABSTRACT: Polyureas (PUs) have already found wide practical applications, and various methods of their synthesis have been reported. In this manuscript, we wished to report the very first mechanochemical approach towards aromatic PUs via reactions between isomeric 2,2'-, 3,3'-, and 4,4'-diaminobiphenyls and triphosgene under solvent-free conditions following ball-milling. By using this synthetic approach, both PUs and azomethine-capped Pus were obtained. The fluorescence response of the above-mentioned PUs towards various anions in solutions were studied and selective fluorescence responses towards the hydroxyl and fluoride anions were observed.

SUBMITTER: Al-Ithawi WKA

PROVIDER: S-EPMC10611254 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Mechanosynthesis of Polyureas and Studies of Their Responses to Anions.

Al-Ithawi Wahab K A WKA Aluru Rammohan R Baklykov Artem V AV Khasanov Albert F AF Kovalev Igor S IS Nikonov Igor L IL Kopchuk Dmitry S DS Novikov Alexander S AS Santra Sougata S Zyryanov Grigory V GV Ranu Brindaban C BC

Polymers 20231020 20

Polyureas (PUs) have already found wide practical applications, and various methods of their synthesis have been reported. In this manuscript, we wished to report the very first mechanochemical approach towards aromatic PUs via reactions between isomeric 2,2'-, 3,3'-, and 4,4'-diaminobiphenyls and triphosgene under solvent-free conditions following ball-milling. By using this synthetic approach, both PUs and azomethine-capped Pus were obtained. The fluorescence response of the above-mentioned PU ...[more]

PMID: 37896404

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Project description:The benzoylcyanoxime, NC-C(=N-OH)-C(O)-C6H5 (later H(BCO)), represents a new ampolydentate ligand that received attention in the light of useful biological properties of its coordination compounds. Colorless H(BCO), upon deprotonation, gains color that depends on the counter-cation and the system in general. Five derivatives of H(BCO), with colorless organic and inorganic mono-cations - Cs, Tl, Ag, N(CH3)4 and As(C6H5)4 - were synthesized and characterized by the X-ray analysis, vibrational and electronic spectroscopy. Compounds exhibited unexpected and significant differences in color, both in solid state and in solutions, that were challenging to explain, thereby warranting detailed investigation including high-level DFT/TDFT computations. It was found that the BCO- anion demonstrates negative solvatochromic in polar protic ROH (R = H, CH3, C2H5, C3H7, C4H9) solvents, and appears yellow in color, as tetraalkylammonium or alkali metal salts. In polar aprotic solvents, such as CH3CN, DMF, and DMSO, solutions of the BCO- anion are red. The color originates from n→π* transition in the anion. Solid state structures evidenced a considerable dependence on planarity of the BCO- anion on its color, as well as on the character of bonding in the C-N-O fragment: yellow color is associated with an oxime (bond length C-N is shorter than N-O), while red color is due to the nitroso character (bond length C-N is longer than the N-O). An addition of ethanol to red solutions of the BCO-containing salts leads to the color change to yellow, which is the result of the formation of an H-bond between the C-N-O fragment of cyanoxime and the solvent, also leading to the flattening of the structure. An explanation for this new color-changing effect was offered, based on experimental evidence and TD/DFT calculations. Glossary: H(BCO) is 1-cyano-1-oximino-acetophenone, or benzoylcyanoxime; BCO- is anion of the benzoylcyanoxime; AsPh4 + is tetraphenylarsonium cation; MMe4 + is tetramethyammonium cation; ROH - alcohols; DMF - dimethylformamide; DMSO - dimethylsulfoxide; AN - acetonitrile; DFT -Density Functional Theory; TDDFT - Time-Dependent Density Functional Theory.

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Mechanosynthesis of Polyureas and Studies of Their Responses to Anions.

Publications

Mechanosynthesis of Polyureas and Studies of Their Responses to Anions.

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