2-acyl-1-aryl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives : versatile fluorescent probes with remarkably large Stokes shift

Petek, Nejc (author), Erjavec, Bibi (author), Slapšak, Dejan (author), Gaber, Aljaž (author), Grošelj, Uroš (author), Požgan, Franc (author), Ričko, Sebastijan (author), Štefane, Bogdan (author), Klemenčič, Marina (author), Svete, Jurij (author)

A series of thirteen 2-acyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives were synthesized by using a copper-catalyzed azomethine-imine-alkyne cycloaddition as a key step. These bimane-related fluorescent compounds with λ$_{ex}$ = 338–400 nm and λ$_{em}$ = 522–644 nm exhibit interesting and promising optical properties, including a remarkably large Stokes shift (150–268 nm), positive solvatochromism, and strong dependence of emission intensity on pH in a range of pH 2–10. The benzotriazolide- and N-succinimidyl ester-functionalized compounds were successfully used as fluorescent probes for protein labelling.

• Language: English
• Keywords: 6, 7-dihydro-1H, 5H-pyrazolo[1, 2-a]pyrazoles, benzotriazolides, fluorescent imaging, bioconjugation, solvatochromism
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2022
• Number of pages: 13 str.
• Numbering: Vol. 201, art. 110224
• PID: 20.500.12556/RUL-137625
• UDC: 547.77
• ISSN on article: 0143-7208
• DOI: 10.1016/j.dyepig.2022.110224
• COBISS.SI-ID: 100346115
• Publication date in RUL: 23.06.2022

Record is a part of a journal

• Title: Dyes and pigments
• Shortened title: Dyes pigm.
• Publisher: Elsevier
• ISSN: 0143-7208
• COBISS.SI-ID: 25357056

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: 6, 7-dihidro-1H, 5H-pirazolo[1, 2-a]pirazoli, benzotriazolidi, fluorescentno označevanje, biokonjugacija, solvatokromija

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0140
• Name: Proteoliza in njena regulacija