NDLI: Parent, Unsubstituted Hemiporphycene: Synthesis and Properties

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Parent, Unsubstituted Hemiporphycene: Synthesis and Properties

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Kijak, Michal Waluk, Jacek Ostapko, Jakub Orzanowska, Grazyna Lesniewska, Barbara Nawara, Krzysztof Pietrzak, Mariusz Buczynska, Joanna
Description	Author Affiliation: Ostapko J ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Nawara K ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Kijak M ( Faculty of Mathematics and Natural Sciences, College of Science, Cardinal Stefan Wyszynski University, Dewajtis 5, 01-815, Warsaw, Poland.); Buczynska J ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Lesniewska B ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Pietrzak M ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Orzanowska G ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.); Waluk J ( Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224, Warsaw, Poland.)
Abstract	Among seven possible nitrogen-in constitutional isomers of porphyrin only one, porphycene, has been obtained so far in the free, unsubstituted form. Herein, the synthesis of another isomer, parent hemiporphycene (HPc), and its thorough structural, spectral, photophysical, electrochemical, and theoretical characterization are reported. Most of the properties of HPc are intermediate between those of porphyrin and porphycene, as evidenced by the values of inner-cavity dimensions, orbital-energy splittings, absorption coefficients, magnetic circular dichroism parameters, NH-stretching frequencies, fluorescence quantum yields, tautomerization rates, and redox potentials. The largest differences arise with respect to tautomerism, due to the low symmetry of HPc and inequivalence of the four nitrogen atoms that define the inner cavity. Two trans tautomers are observed, separated in energy by about $1 kcal mol^{−1}.$ Tautomerization from the higher- to the lower-energy form is detected in the lowest-excited singlet state and occurs at a rate that is about four orders of magnitude lower than that observed for porphycene. Hemiporphycene is a very good model for the investigation of inequivalent intramolecular H-bonds present in one molecule; two such bonds in HPc reveal unusual characteristics, and the bond strength results from the interplay between the N⋅⋅⋅N distance and the N−H−N angle.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	48
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-11-21
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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