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Synthesis 2024; 56(12): 1896-1904
DOI: 10.1055/s-0042-1751561
paper

Synthesis, Photophysical, and AIE Properties of 2H-Imidazole-Derived Push-Pull Fluorophores

Igor A. Lavrinchenko
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Egor A. Nikiforov
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Timofey D. Moseev 
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Mikhail V. Varaksin  ∗
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Anton N. Tsmokalyuk
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Thomas V. Nechaev
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
,
Valery N. Charushin
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
,
Oleg N. Chupakhin  ∗
a   Ural Federal University, 19 Mira Str., 620002 Ekaterinburg, Russian Federation
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskaya Str., 620990 Ekaterinburg, Russian Federation
› Author AffiliationsThe research was financially supported by the Russian Science Foundation (RSF), project No. 20-73-10077, https://www.rscf.ru/en/project/20-73-10077/ (chemical synthesis and photophysical studies) and by the Ministry of Science and Higher Education of the Russian Federation within the Priority-2030 Program of Ural Federal University (conceptualization).
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Abstract

A four-stage method for the synthesis of 2H-imidazole-derived push-pull fluorophores was developed. The synthesized compounds are characterized by absorption in the range of 250–400 nm, emission of up to 617 nm, and quantum yields of up to 99%. Compounds bearing a tetraphenylethylene fragment demonstrated the AIE effect in a solution with a water fraction fw >90% and significant increase in the emission intensity of up to 20 times and quantum yields of up to 22%. The ICT states for these fluorophores were confirmed by calculating the excited state dipole moments (>23D). The reported synthetic method enables fine-tuning of the fluorescent properties for the developed photoactive molecular systems by varying donor fragments. The obtained compounds could be of particular interest in the design of photoactive organic and hybrid materials.

Key words

fluorophore - imidazole - aggregation induced emission - Suzuki–Miyaura coupling - photoredox-catalyzed deoxygenation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751561.
  • Supporting Information


Publication History

Received: 12 December 2023

Accepted after revision: 02 February 2024

Article published online:
22 February 2024

© 2024. Thieme. All rights reserved

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  • References

    • 1a Malytskyi V, Simon J.-J, Patrone L, Raimundo J.-M. RSC Adv. 2015; 5: 354
      Crossref
    • 1b Pigot C, Noirbent G, Brunel D, Dumur F. Eur. Polym. J. 2020; 133: 109797
      Crossref
    • 1c Verbitskiy EV, Rusinov GL, Chupakhin ON, Charushin VN. Dyes Pigm. 2020; 180: 108414
      Crossref
    • 1d Kaur P, Singh K. Chem. Rec. 2022; 22: e202200024
      CrossrefPubMed
    • 1e Patil Y, Butenschön H, Misra R. Chem. Rec. 2023; 23: e202200208
      CrossrefPubMed
    • 1f Kulhánek J, Bureš F. Beilstein J. Org. Chem. 2012; 8: 25
      CrossrefPubMed
    • 2a Bureš F. RSC Adv. 2014; 4: 58826
      Crossref
    • 2b Ko HM, Choi H, Paek S, Kim K, Song K, Lee JK, Ko J. J. Mater. Chem. 2011; 21: 7248
      Crossref
    • 2c Samanta PK, Misra R. J. Appl. Phys. 2023; 133: 020901
      Crossref
    • 2d Liu J, Gao W, Kityk IV, Liu X, Zhen Z. Dyes Pigm. 2015; 122: 74
      Crossref
    • 2e Braveenth R, Chai KY. Materials (Basel) 2019; 12: 2646
      CrossrefPubMed
    • 2f Han J, Chen Y, Li N, Huang Z, Yang C. Aggregate 2022; 3: e182
      Crossref
    • 3a Hao M, Chi W, Wang C, Xu Z, Li Z, Liu X. J. Phys. Chem. C 2020; 124: 16820
      Crossref
    • 3b Niu H, Liu J, O’Connor HM, Gunnlaugsson T, James TD, Zhang H. Chem. Soc. Rev. 2023; 52: 2322
      CrossrefPubMed
    • 3c Wang H, Zhao E, Lam JW. Y, Tang BZ. Mater. Today 2015; 18: 365
      Crossref
    • 3d Sasaki S, Drummen GP. C, Konishi G. J. Mater. Chem. C 2016; 4: 2731
      Crossref
    • 3e Giel M, Hong Y. Aggregate 2023; 4: e336
      Crossref
    • 4a Kachwal V, Tan J. Adv. Sci. (Weinh) 2023; 10: 2204848
      CrossrefPubMed
    • 4b Das AK, Goswami S. Sens. Actuators B Chem. 2017; 245: 1062
      Crossref
    • 4c Sharath Kumar KS, Girish YR, Ashrafizadeh M, Mirzaei S, Rakesh KP, Hossein Gholami M, Zabolian A, Hushmandi K, Orive G, Kadumudi FB, Dolatshahi-Pirouz A, Thakur VK, Zarrabi A, Makvandi P, Rangappa KS. Coord. Chem. Rev. 2021; 447: 214135
      Crossref
    • 4d Hong Y. Methods Appl. Fluoresc. 2016; 4: 022003
      CrossrefPubMed
    • 7a Ilhan H, Cakmak Y. Top. Curr. Chem. 2023; 381: 28
      CrossrefPubMed
    • 7b Feng X, Wei L, Liu Y, Chen X, Tian R. Adv. Healthc. Mater. 2023; 12: e2300537
      CrossrefPubMed
    • 7c Zhang J, Zhou M, Li X, Fan Y, Li J, Lu K, Wen H, Ren J. Talanta 2023; 254: 124133
      CrossrefPubMed
    • 7d Olesińska-Mönch M, Deo C. Chem. Commun. 2023; 59: 660
      CrossrefPubMed
    • 7e Wang Z, Ma J, Li C, Zhang H. Biosensors 2023; 13: 159
      CrossrefPubMed
    • 7f Zhou H, Ren T. Chem. Asian J. 2022; 17: e202200147
      CrossrefPubMed
    • 7g Hande PE, Shelke YG, Datta A, Gharpure SJ. ChemBioChem 2022; 23: e202100448
      CrossrefPubMed
    • 7h Wang K, Zhang J, Hu R, Liu C, Bartholome TA, Ge H, Li B. ACS Catal. 2022; 12: 2796
      Crossref
    • 7i Neto BA. D, Correa JR, Spencer J. Chem. Eur. J. 2022; 28: e202103262
      CrossrefPubMed
    • 7j Riahin C, Mendis K, Busick B, Ptaszek M, Yang M, Stacey G, Parvate A, Evans JE, Traeger J, Hu D, Orr G, Rosenzweig Z. Sensors 2022; 22: 7218
      CrossrefPubMed
    • 7k Dong L, Peng H.-Q, Niu L.-Y, Yang Q.-Z. Top. Curr. Chem. 2021; 379: 18
      CrossrefPubMed
    • 8a Lama AD, Sestelo JP, Valencia L, Esteban-Gomez D, Sarandeses LA, Martinez MM. Dyes Pigm. 2022; 205: 110539
      Crossref
    • 8b Chen G, Qiu Z, Tan J.-H, Chen W.-C, Zhou P, Xing L, Ji S, Qin Y, Zhao Z, Huo Y. Dyes Pigm. 2021; 184: 108754
      Crossref
    • 8c Dey N, Kulhánek J, Bures F, Bhattacharya S. J. Org. Chem. 2021; 86: 14663
      CrossrefPubMed
    • 8d Hloušková Z, Bures F. ARKIVOC 2017; (iv): 330
      Crossref
  • 9 Moseev TD, Varaksin MV, Virlova EA, Medvedeva MV, Svalova TS, Melekhin VV, Tsmokaluk AN, Kozitsina AN, Charushin VN, Chupakhin ON. Dyes Pigm. 2022; 202: 110251
    Crossref
    • 10a Farhang M, Akbarzadeh AR, Rabbani M, Ghadiri AM. Polyhedron 2022; 227: 116124
      CrossrefPubMed
    • 10b D’Alterio MC, Casals-Cruañas È, Tzouras NV, Talarico G, Nolan SP, Poater A. Chem. Eur. J. 2021; 27: 13481
      CrossrefPubMed
  • 11 Kim SH, An JH, Lee JH. Org. Biomol. Chem. 2021; 19: 3735
    CrossrefPubMed
  • 12 Lakowicz JR, Masters BR. J. Biomed. Opt. 2008; 13: 029901
    Crossref
  • 13 Porrès L, Holland A, Pålsson L.-O, Monkman AP, Kemp C, Beeby A. J. Fluoresc. 2006; 16: 267
    CrossrefPubMed
    • 14a Moseev TD, Varaksin MV, Gorlov DA, Charushin VN, Chupakhin ON. J. Org. Chem. 2020; 85: 11124
      CrossrefPubMed
    • 14b Lavrinchenko IA, Moseev TD, Seleznev YA, Varaksin MV, Tsmokaluk AN, Charushin VN, Chupakhin ON. Asian J. Org. Chem. 2023; 12: e202300008
      Crossref
  • 15 Smyshliaeva LA, Varaksin MV, Slepukhin PA, Chupakhin ON, Charushin VN. Beilstein J. Org. Chem. 2018; 14: 2618
    CrossrefPubMed
  • 16 Zhao Z, Chen S, Lam JW. Y, Lu P, Zhong Y, Wong KS, Kwok HS, Tang BZ. Chem. Commun. 2010; 46: 2221
    CrossrefPubMed