Synthesis and Characterization of Bulky Substituted Hemihexaphyrazines Bearing 2,6-Diisopropylphenoxy Groups

Evgenii N Ivanov; Verónica Almeida-Marrero; Oskar I Koifman; Viktor V Aleksandriiskii; Tomas Torres; Mikhail K Islyaikin

doi:10.3390/molecules28155740

Synthesis and Characterization of Bulky Substituted Hemihexaphyrazines Bearing 2,6-Diisopropylphenoxy Groups

Molecules. 2023 Jul 29;28(15):5740. doi: 10.3390/molecules28155740.

Authors

Evgenii N Ivanov^{1

2}, Verónica Almeida-Marrero³, Oskar I Koifman^{1

2}, Viktor V Aleksandriiskii^{1

2}, Tomas Torres^{3

4

5}, Mikhail K Islyaikin^{1

2}

Affiliations

¹ IRLoN, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 7, Sheremetievskiy Ave., 153000 Ivanovo, Russia.
² G. A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Str., 153045 Ivanovo, Russia.
³ Department of Organic Chemistry, Autonoma University of Madrid, Cantoblanco, 28049 Madrid, Spain.
⁴ Institute for Advanced Research in Chemical Sciences (IAdChem), Autonoma University of Madrid, 28049 Madrid, Spain.
⁵ Instituto Madrileño de Estudios Avanzados (IMDEA)-Nanociencia, c/Faraday 9, Cantoblanco, 28049 Madrid, Spain.

Abstract

New substituted [30]trithiadodecaazahexaphyrines (hemihexaphyrazines) were synthesized by a crossover condensation of 2,5-diamino-1,3,4-thiadiazole with 4-chloro-5-(2,6-diisopropylphenoxy)- or 4,5-bis-(2,6-diisopropylphenoxy)phthalonitriles. The compounds were characterized by ¹H-, ¹³C-NMR, including COSY, HMBC, and HSQC spectroscopy, MALDI TOF spectrometry, elemental analysis, IR and UV-Vis absorbance and fluorescence techniques.

Keywords: 2,5-diamino-1,3,4-thiadiazole; expanded hemiporphyrazines; hemihexaphyrazines.

Grants and funding

This work was financially supported by a Grant from the Ministry of Science and Higher Education of the Russian Federation [No. 075-15-2021-579] (DFT calculations). In particular, the study was carried out using the resources of the Center for Shared Use of Scientific Equipment of the ISUCT (N. 075-15-2021-671). T.T. acknowledges financial support from MICINN (PID 2020-116490GB-I00 and TED 2021-131255B-C43) and the Comunidad de Madrid and the Spanish State through the Recovery, Transformation and Resilience Plan [“Materiales Disruptivos Bidimensionales (2D)” (MAD2D-CM) (UAM1)-MRR Materiales Avanzados] and the European Union through the Next Generation EU funds. IMDEA Nanociencia acknowledges support from the “Severo Ochoa” Programme for Centres of Excellence in R & D (MINECO, Grant SEV 2016-0686). We also thank the Institute for Advanced Research in Chemical Sciences (IAdChem), Autonoma University of Madrid, Madrid, for the facilities provided.