Λεπτομέρειες βιβλιογραφικής εγγραφής
| Τίτλος: |
Hydrolytic Cleavage and Deborylation of Boron(III) Subphthalocyanines─A Synthetic Approach to Fused Diazatripyrrins. |
| Συγγραφείς: |
Fazlyeva AM; Department of Organic Chemistry, Ivanovo State University of Chemistry and Technology (ISUCT), Ivanovo RF-153000, Russia., Skvortsov IA; Department of Organic Chemistry, Ivanovo State University of Chemistry and Technology (ISUCT), Ivanovo RF-153000, Russia., Somov NV; Department of Crystallography and Experimental Physics, Lobachevsky State University, Nizhnij Novgorod, RF-603950, Russia., Stuzhin PA; Department of Organic Chemistry, Ivanovo State University of Chemistry and Technology (ISUCT), Ivanovo RF-153000, Russia. |
| Πηγή: |
Inorganic chemistry [Inorg Chem] 2025 Sep 29; Vol. 64 (38), pp. 19197-19206. Date of Electronic Publication: 2025 Jul 23. |
| Τύπος έκδοσης: |
Journal Article |
| Γλώσσα: |
English |
| Στοιχεία περιοδικού: |
Publisher: American Chemical Society Country of Publication: United States NLM ID: 0366543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-510X (Electronic) Linking ISSN: 00201669 NLM ISO Abbreviation: Inorg Chem Subsets: MEDLINE; PubMed not MEDLINE |
| Imprint Name(s): |
Original Publication: [Easton, Pa.] American Chemical Society. |
| Περίληψη: |
Boron(III) subphthalocyanine analogues with enhanced electron affinity in the presence of water undergo hydrolytic cleavage of the macrocycle and deborylation, resulting in formation of noncyclic aza-bridged tris-isoindoles, which are fused derivatives of 5,10-diazatripyrrines (DATRIPY). Spectral data, kinetic studies, and DFT results allow us to suggest a plausible mechanism of DATRIPY formation, which includes nucleophilic addition of water to one of the CαNmeso bonds and its rupture as a key stage. This reaction is possible for perhalogenated or/and azasubstituted boron(III) subphthalocyanine analogues and occurs especially easily for hexachlorinated tripyrazinosubporphyrazinatoboron(III) chloride, affording the corresponding 14-amino-5,10-diazatripyrrin-1-one [DATRIPY1a] bearing fused dichloropyrazine fragments in each pyrrole unit. An X-ray diffraction study revealed that DATRIPY1a has an S-like conformation, which is stabilized by two intramolecular hydrogen bonds between pyrrolic NH groups and pyrrolenine and pyrazine nitrogens. DATRIPY1a reacts with BF3, forming a noncyclic tripyrrolic bis-boron(III) complex [BODATRIPY] in which two BF2 fragments are bonded by pyrrole-pyrrolenine and pyrrole-pyrazine coordination sites. Due to rearrangement of intramolecular H-bonds occurring in aprotic and proton donor solvents, DATRIPY1a exhibits strong solvatochromism and can also be used as a colorimetric sensor for the presence of hard anions (fluoride, hydroxide, cyanide, and cyanate). |
| Entry Date(s): |
Date Created: 20250723 Latest Revision: 20250929 |
| Update Code: |
20260130 |
| DOI: |
10.1021/acs.inorgchem.5c02123 |
| PMID: |
40701948 |
| Βάση Δεδομένων: |
MEDLINE |