Morasi Piperčić, Sara; Bjelopetrović, Alen; Juribašić Kulcsar, Marina (2025) Mechanochemical Synthesis and Optical Properties of Solvatochromic 2H-Indazole-3,5-diones. Dyes and Pigments, 243 . ISSN 0143-7208
![[img]](http://fulir.irb.hr/style/images/fileicons/application_pdf.png) |
PDF
- Accepted Version
- article
Restricted to Closed Access until 21 July 2027. Download (2MB) | Request a personal copy from author |
Abstract
Mechanochemical synthesis of 4-hydroxyazobenzene-2-carboxylic acids and their cyclization to highly-functionalized chromophores, 2-aryl-4-(arylamino)-2H-indazole-3,5-diones, is reported. Mechanism of the cyclization is suggested and supported by DFT calculations. Optical properties of azobenzenes and indazoles have been studied in solution and in the solid state using UV-vis spectroscopy, and in silico by DFT calculations. 2H-indazole-3,5-diones strongly absorb above 400 nm and show a negative solvatochromic behavior. Computational analysis of the ground-state photophysical properties for the 2H-indazole-3,5-diones showed that they are a donor-acceptor-donor (D-A-D’) system where two donor substituents (D and D’, 2-aryl and 4-arylamino groups) transfer their electron density to the central acceptor 2H-indazole unit (A).
| Item Type: | Article | ||||||||
|---|---|---|---|---|---|---|---|---|---|
| Additional Information: | SMP i AP jednako su doprinijeli ovom radu. | ||||||||
| Uncontrolled Keywords: | indazole; mechanochemistry; DFT calculations; UV-vis spectroscopy; solvatochromism; mechanism | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry > Organic Chemistry | ||||||||
| Divisions: | Division of Physical Chemistry | ||||||||
| Projects: |
|
||||||||
| Depositing User: | Marina Juribašić Kulcsar | ||||||||
| Date Deposited: | 28 Jul 2025 13:41 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/9914 | ||||||||
| DOI: | 10.1016/j.dyepig.2025.113044 |
Actions (login required)
 |
View Item |
Altmetric
Altmetric
