Phenyl-2-benzothiazole-based α-aminophosphines: Synthesis, crystal structure, and photophysical properties

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Phenyl-2-benzothiazole-based α-aminophosphines: Synthesis, crystal structure, and photophysical properties. / Sukhikh, T. S.; Kolybalov, D. S.; Khisamov, R. M. et al.

In: Journal of Structural Chemistry, Vol. 63, No. 9, 09.2022, p. 1446-1452.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{b9b93d75bf834a23a937629ef9a2f4a2,

title = "Phenyl-2-benzothiazole-based α-aminophosphines: Synthesis, crystal structure, and photophysical properties",

abstract = "Condensation reactions of diphenylphosphine, 2-(benzo[d]thiazol-2-yl)aniline (NH2-pbt) and a series of aldehydes RC(O)H (R = phenyl, 2-furanyl and 4-pyridyl) are carried out to obtain α-aminophosphines Ph2P(O)C(R)NH-pbt. In the case of phenyl and 2-furanyl derivatives, respective compounds 1 and 2 are isolated with a yield of 80-85%, and 4-pyridyl analogue 3 is obtained in an insignificant amount. According to single crystal X-ray diffraction data, the compounds crystallize in the chiral space group P212121, forming crystals containing only R- or S-enantiomers. Additional substituents R do not strongly affect the spatial geometry of molecules. The photophysical properties of compounds 1 and 2 are similar, and this means that the additional substituents contribute equally to the character of electronic transitions in the compounds.",

keywords = "aminophosphines, luminescence, phospha-Mannich reactions, thiazole",

author = "Sukhikh, {T. S.} and Kolybalov, {D. S.} and Khisamov, {R. M.} and Konchenko, {S. N.}",

note = "Funding Information: The work was supported by the Russian Science Foundation (project No. 21-73-10096). Luminescent studies were supported by the Ministry of Science and Higher Education of the Russian Federation (No. 121031700321-3). Publisher Copyright: {\textcopyright} 2022, Pleiades Publishing, Ltd.",

year = "2022",

month = sep,

doi = "10.1134/S0022476622090074",

language = "English",

volume = "63",

pages = "1446--1452",

journal = "Journal of Structural Chemistry",

issn = "0022-4766",

publisher = "Springer GmbH & Co, Auslieferungs-Gesellschaf",

number = "9",

}

RIS

TY - JOUR

T1 - Phenyl-2-benzothiazole-based α-aminophosphines: Synthesis, crystal structure, and photophysical properties

AU - Sukhikh, T. S.

AU - Kolybalov, D. S.

AU - Khisamov, R. M.

AU - Konchenko, S. N.

N1 - Funding Information: The work was supported by the Russian Science Foundation (project No. 21-73-10096). Luminescent studies were supported by the Ministry of Science and Higher Education of the Russian Federation (No. 121031700321-3). Publisher Copyright: © 2022, Pleiades Publishing, Ltd.

PY - 2022/9

Y1 - 2022/9

N2 - Condensation reactions of diphenylphosphine, 2-(benzo[d]thiazol-2-yl)aniline (NH2-pbt) and a series of aldehydes RC(O)H (R = phenyl, 2-furanyl and 4-pyridyl) are carried out to obtain α-aminophosphines Ph2P(O)C(R)NH-pbt. In the case of phenyl and 2-furanyl derivatives, respective compounds 1 and 2 are isolated with a yield of 80-85%, and 4-pyridyl analogue 3 is obtained in an insignificant amount. According to single crystal X-ray diffraction data, the compounds crystallize in the chiral space group P212121, forming crystals containing only R- or S-enantiomers. Additional substituents R do not strongly affect the spatial geometry of molecules. The photophysical properties of compounds 1 and 2 are similar, and this means that the additional substituents contribute equally to the character of electronic transitions in the compounds.

AB - Condensation reactions of diphenylphosphine, 2-(benzo[d]thiazol-2-yl)aniline (NH2-pbt) and a series of aldehydes RC(O)H (R = phenyl, 2-furanyl and 4-pyridyl) are carried out to obtain α-aminophosphines Ph2P(O)C(R)NH-pbt. In the case of phenyl and 2-furanyl derivatives, respective compounds 1 and 2 are isolated with a yield of 80-85%, and 4-pyridyl analogue 3 is obtained in an insignificant amount. According to single crystal X-ray diffraction data, the compounds crystallize in the chiral space group P212121, forming crystals containing only R- or S-enantiomers. Additional substituents R do not strongly affect the spatial geometry of molecules. The photophysical properties of compounds 1 and 2 are similar, and this means that the additional substituents contribute equally to the character of electronic transitions in the compounds.

KW - aminophosphines

KW - luminescence

KW - phospha-Mannich reactions

KW - thiazole

UR - http://www.scopus.com/inward/record.url?scp=85139407352&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/4d238037-1257-35b2-ac30-6db5d2447949/

U2 - 10.1134/S0022476622090074

DO - 10.1134/S0022476622090074

M3 - Article

AN - SCOPUS:85139407352

VL - 63

SP - 1446

EP - 1452

JO - Journal of Structural Chemistry

JF - Journal of Structural Chemistry

SN - 0022-4766

IS - 9

ER -

ID: 38153590