Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one

Standard

Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one. / POTAPOV, D.A.; SONINA, A.A.; BECKER, C.S. et al.

In: Chemistry for Sustainable Development, Vol. 33, No. 5, 9, 2025, p. 562-569.

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

Author

POTAPOV, D.A. ; SONINA, A.A. ; BECKER, C.S. et al. / Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one. In: Chemistry for Sustainable Development. 2025 ; Vol. 33, No. 5. pp. 562-569.

BibTeX

@article{88a6863a3b9d4a928d0a91dd0d8918df,

title = "Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one",

abstract = "2,7-Di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one (TDAFO) was synthesised and its crystal structure, optical and electrochemical properties were studied. The target compound was obtained using the Stille reaction from 2-(tri(n-butylstannyl)thiophene and 2,7-dibromo-4,5-diazafluoren-9-one. Using X-ray diffraction analysis, the crystal structure of TDAFO was solved, and the formation of weak π-stacking interactions, C-H···N and C-H···O hydrogen bonds was revealed. The oxidation and reduction potentials of TDAFO were evaluated by cyclic voltammetry, and the possibility of TDAFO electropolymerisation on conductive coatings was demonstrated. The optical properties of both the monomer and the polymer obtained by electrochemical polymerisation were studied. The photoluminescence quantum yield of TDAFO was determined to be 7 % in solution and 13 % in the crystalline form.",

keywords = "4,5-DIAZAFLUORENE, CROSS-COUPLING, PHOTOLUMINESCENCE, ELECTROPOLYMERISATION",

author = "D.A. POTAPOV and A.A. SONINA and C.S. BECKER and M.S. KAZANTSEV",

note = "Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one / D. A. Potapov, A. A. Sonina, C. S. Becker, M. S. Kazantsev // Chemistry for Sustainable Development. – 2025. – Vol. 33, No. 5. – P. 562-569. – DOI 10.15372/CSD2025689. – EDN WCAAGC. The work was supported by the Russian Science Foundation, Project No. 23-73-10015, https://rscf.ru/project/23-73-10015/.",

year = "2025",

doi = "10.15372/csd2025689",

language = "English",

volume = "33",

pages = "562--569",

journal = "Chemistry for Sustainable Development",

issn = "1817-1818",

publisher = "ФГУП {"}Издательство СО РАН{"}",

number = "5",

}

RIS

TY - JOUR

T1 - Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one

AU - POTAPOV, D.A.

AU - SONINA, A.A.

AU - BECKER, C.S.

AU - KAZANTSEV, M.S.

N1 - Synthesis and physicochemical properties of 2,7-di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one / D. A. Potapov, A. A. Sonina, C. S. Becker, M. S. Kazantsev // Chemistry for Sustainable Development. – 2025. – Vol. 33, No. 5. – P. 562-569. – DOI 10.15372/CSD2025689. – EDN WCAAGC. The work was supported by the Russian Science Foundation, Project No. 23-73-10015, https://rscf.ru/project/23-73-10015/.

PY - 2025

Y1 - 2025

N2 - 2,7-Di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one (TDAFO) was synthesised and its crystal structure, optical and electrochemical properties were studied. The target compound was obtained using the Stille reaction from 2-(tri(n-butylstannyl)thiophene and 2,7-dibromo-4,5-diazafluoren-9-one. Using X-ray diffraction analysis, the crystal structure of TDAFO was solved, and the formation of weak π-stacking interactions, C-H···N and C-H···O hydrogen bonds was revealed. The oxidation and reduction potentials of TDAFO were evaluated by cyclic voltammetry, and the possibility of TDAFO electropolymerisation on conductive coatings was demonstrated. The optical properties of both the monomer and the polymer obtained by electrochemical polymerisation were studied. The photoluminescence quantum yield of TDAFO was determined to be 7 % in solution and 13 % in the crystalline form.

AB - 2,7-Di(thiophen-2-yl)-9H-(4,5-diazafluoren)-9-one (TDAFO) was synthesised and its crystal structure, optical and electrochemical properties were studied. The target compound was obtained using the Stille reaction from 2-(tri(n-butylstannyl)thiophene and 2,7-dibromo-4,5-diazafluoren-9-one. Using X-ray diffraction analysis, the crystal structure of TDAFO was solved, and the formation of weak π-stacking interactions, C-H···N and C-H···O hydrogen bonds was revealed. The oxidation and reduction potentials of TDAFO were evaluated by cyclic voltammetry, and the possibility of TDAFO electropolymerisation on conductive coatings was demonstrated. The optical properties of both the monomer and the polymer obtained by electrochemical polymerisation were studied. The photoluminescence quantum yield of TDAFO was determined to be 7 % in solution and 13 % in the crystalline form.

KW - 4,5-DIAZAFLUORENE

KW - CROSS-COUPLING

KW - PHOTOLUMINESCENCE

KW - ELECTROPOLYMERISATION

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001677417100001

UR - https://www.elibrary.ru/item.asp?id=88834909

UR - https://www.mendeley.com/catalogue/bf93b3ad-d1de-3db1-ae43-ab6a64a1b7d7/

U2 - 10.15372/csd2025689

DO - 10.15372/csd2025689

M3 - Article

VL - 33

SP - 562

EP - 569

JO - Chemistry for Sustainable Development

JF - Chemistry for Sustainable Development

SN - 1817-1818

IS - 5

M1 - 9

ER -

ID: 83183501