Novel benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) electron-withdrawing building block for the design of materials with tunable photophysical properties and highly efficient luminescence

Novel benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) electron-withdrawing building block for the design of materials with tunable photophysical properties and highly efficient luminescence Full article

Journal

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
ISSN: 1386-1425 , E-ISSN: 1873-3557

Output data

Year: 2027, Volume: 365, Article number : 128692, Pages count : DOI: 10.1016/j.saa.2026.128692

Authors

Korshunov Vladislav M. ^1,2 , Chmovzh Timofey N. ³ , Melnikova Anna M. ¹ , Tsorieva Alisia V. ² , Ferulev Alexey I. ² , Kulikova Ekaterina A. ^4,3 , Trainov Konstantin P. ³ , Belyy Alexander Y. ³ , Mikhalchenko Ludmila V. ³ , Taydakov Ilya V. ^5,2 , Rakitin Oleg A. ³

Affiliations

1	Bauman Moscow State Technical University, 5/1 2-ya Baumanskaya Str., 105005 Moscow, Russia
2	P. N. Lebedev Physical Institute of the Russian Academy of Sciences, 119991 Moscow, Russia
3	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russia
4	D. I. Mendeleev University of Chemistry and Technology of Russia, Miusskaya sqr., 9, Moscow 125047, Russian Federation
5	G.V. Plekhanov Russian University of Economics, Stremyanny per. 36, Moscow 117997, Russian Federation

Symmetric and asymmetric D-Asingle bondD′ derivatives based on the benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) moiety with different donor groups were synthesized. Symmetric dyes were prepared from benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) by palladium catalyzed Csingle bondH (het)arylation reaction. Asymmetric molecules were synthesized from 4-bromobenzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) by two consecutive cross-coupling reactions: direct Csingle bondH (het)arylation and Suzuki-Miyaura reaction. Symmetric molecules were shown to exhibit higher emission quantum yields (up to 86%) compared to their asymmetric counterparts due to dual excitation pathways. Time-resolved fluorescence studies revealed two emitting excited states for symmetric 4,8-di(thiophen-2-yl)benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole): intramolecular charge transfer and locally excited states. The photoluminescence efficiency of symmetric dyes exhibits a weak dependence on the solvent nature, maintaining high values in both polar and low-polar environments. The obtained data correlate well with the results of quantum chemical calculations. Thus, symmetric D-A-D molecules based on [benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) may be useful in the design of promising highly luminescent materials.

Korshunov V.M. , Chmovzh T.N. , Melnikova A.M. , Tsorieva A.V. , Ferulev A.I. , Kulikova E.A. , Trainov K.P. , Belyy A.Y. , Mikhalchenko L.V. , Taydakov I.V. , Rakitin O.A.
Novel benzo[1,2-d:4,5-d']bis([1,2,3]thiadiazole) electron-withdrawing building block for the design of materials with tunable photophysical properties and highly efficient luminescence
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2027. V.365. 128692 . DOI: 10.1016/j.saa.2026.128692 Scopus OpenAlex

Submitted:	Jun 29, 2026
Published online:	Sep 5, 2026

≡ Scopus:	2-s2.0-105049156665
≡ OpenAlex:	W7204795171