Controlling Emissive Properties by Intramolecular Hydrogen Bonds: Alkyl and Aryl <i>meso</i>‐Substituted Porphycenes

Listkowski, Arkadiusz; Masiera, Natalia; Kijak, Michał; Luboradzki, Roman; Leśniewska, Barbara; Waluk, Jacek

doi:10.1002/chem.202005440

Cited by 11 publications

(25 citation statements)

References 34 publications

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“…Among a wide range of π-conjugated molecular receptors such as, e.g., truxenes, − porphycenes, hemiporphycenes, , and corrphycenes, calix[4]arenes are mostly bowl-shaped macrocycles possessing a 3D cavity which is able to accommodate guest molecules inside. Calixarene molecules are based on phenyl rings connected by metyhlene bridges, and they may be successfully modified on their upper or/and lower rims as well as on the benzene rings. − Calixarenes possess a variety of properties, including catalytic, ions transport, luminescence, and adsorption, and they can also act as carriers for drugs and other biologically active substances.…”

Section: Introductionmentioning

confidence: 99%

Host–Guest Complexation of the para-Sulfonato-calix[4]arene Receptor with Biomolecules

Leśniewska

Coleman

Suwińska

2022

Crystal Growth & Design

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arene has been shown to be an excellent receptor for many biomolecules. Here we present four complexes of parasulfonato-calix[4]arene with bioactive molecules, i.e., 2-aminobenzimidazole, thiamine, spermine, and streptidine. Structures of the obtained crystalline complexes were determined by X-ray diffraction. The first three biomolecules are accommodated inside the hydrophobic cavity of the receptor, according to the lock-and-key model. The fourth guest (streptidine) loses the competition for a place inside the calixarene anion with solvent molecules. The presence of Zundel and hydronium cations was experimentally evidenced in the complex with thiamine. A range of noncovalent interactions cementing the structures were identified, including anion−π interactions. The studied compounds are mostly self-assembled in a bilayer fashion.

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Section: Introductionmentioning

confidence: 99%

Host–Guest Complexation of the para-Sulfonato-calix[4]arene Receptor with Biomolecules

Leśniewska

Coleman

Suwińska

2022

Crystal Growth & Design

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“…with N…N distance. [48][49][50][51][52] It has also been shown that a properly selected substitution changes the geometry of the porphyrin cavity, bringing its dimensions closer to that of porphycene. As a result of the change in the cavity geometry, an acceleration of hydrogen transfer by orders of magnitude was observed.…”

Section: Introductionmentioning

confidence: 99%

Correlations of geometric and spectroscopic parameters of intramolecular hydrogen bonds in porphyrin-like macrocycles

Gawinkowski

Prakash

2022

Preprint

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Chemical bond lengths and angles are characteristic structural parameters that describe a molecule. Likewise, the frequencies of the vibration modes and the NMR chemical shift are unique and referred to as "chemical fingerprints" specific to the compound. These are the basic parameters describing and allowing the identification of newly obtained compounds. In macrocyclic compounds with a porphyrin-like structure, intramolecular hydrogen bonding significantly influences the physicochemical properties. This paper presents the correlations between geometric and spectroscopic parameters related to hydrogen bonds in this type of macrocyclic compound. In particular, these relationships were demonstrated for a large group of porphyrin, porphycene, and dibenzotetraaza[14]annulene derivatives and the group of other macrocycles with a similar structure. A very strong linear relationship is found between the frequencies of vibrations of the NH groups of the hydrogen bond and the length of this bond, which is common for all macrocyclic compounds of this type. Several other relationships are shown between spectroscopic (IR, Raman, NMR) and geometric (X-ray) parameters indicating differences and similarities between different families of macrocycles. Apart from a better understanding of the nature of hydrogen bonds and their characteristics in porphyrin-like macrocyclic compounds, these relationships will facilitate the identification of new macrocycles and the extrapolation of their spectroscopic properties.

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“…For example, previous studies have revealed correlations between electronic properties such as fluorescence quantum yield or tautomerisation rate and the hydrogen bond parameters of porphycenes, e.g., the N…N distance. [48][49][50][51][52] It has also been shown that properly selected substituents can alter the geometry of the porphyrin cavity, bringing its dimensions closer to those of porphycene. As a result of a change in cavity geometry, the hydrogen transfer rate was observed to increase by several orders of magnitude.…”

Section: Introductionmentioning

confidence: 99%

Searching for correlations between geometric and spectroscopic parameters of intramolecular hydrogen bonds in porphyrin-like macrocycles

Gawinkowski

Prakash

2022

Preprint

View full text Add to dashboard Cite

Chemical bond lengths and angles are characteristic structural parameters of a molecule. Similarly, the frequencies of the vibrational modes and the NMR chemical shifts are unique "chemical fingerprints" specific to a compound. These are the basic parameters describing newly obtained compounds and enabling their identification. Intramolecular hydrogen bonding significantly influences the physicochemical properties of macrocyclic compounds with a porphyrin-like structure. This work presents the verification for correlations between geometric and spectroscopic parameters related to hydrogen bonds in this type of macrocyclic compounds. In particular, such relationships were investigated for a large group of porphyrin, porphycene, and dibenzotetraaza[14]annulene derivatives and a group of other macrocycles with similar structure. A very strong linear correlation was found only between the vibrational frequencies of the NH groups involved in a hydrogen bond and the length of this bond, which applied to all macrocyclic compounds of this type. Several other relationships were found between spectroscopic (IR, Raman, NMR) and geometric (X-ray) parameters, highlighting differences and similarities between different families of macrocycles. Apart from providing a better understanding of the nature of hydrogen bonds and their characteristics in porphyrin-like macrocyclic compounds, these relationships will facilitate the identification of new macrocycles and the extrapolation of their spectroscopic properties.

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Controlling Emissive Properties by Intramolecular Hydrogen Bonds: Alkyl and Aryl meso‐Substituted Porphycenes

Cited by 11 publications

References 34 publications

Host–Guest Complexation of the para-Sulfonato-calix[4]arene Receptor with Biomolecules

Host–Guest Complexation of the para-Sulfonato-calix[4]arene Receptor with Biomolecules

Correlations of geometric and spectroscopic parameters of intramolecular hydrogen bonds in porphyrin-like macrocycles

Searching for correlations between geometric and spectroscopic parameters of intramolecular hydrogen bonds in porphyrin-like macrocycles

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