Aggregation phenomena in photobicyclised pyridinium salts

Aracena, Andrés; Rezende, Marcos Caroli; Encinas, M. V.; Vergara, Cesar; Vásquez, S.

doi:10.1039/c7nj02788e

Cited by 7 publications

(10 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It should be noted that the 1 H‐NMR signals of a saturated solution of 3 in CD 3 CN are not only much broader but also significantly shifted upfield (Figure S3) in comparison to the signals that were detected after the irradiation of a 2 m M solution of 2c (Figure , 30 minutes). We attribute this to the formation of dye aggregates at higher concentrations, as commonly observed for positively charged, heterocyclic systems …”

Section: Resultsmentioning

confidence: 99%

Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives

Pithan

Ihmels

2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

The photoreactivity of four 8‐styryl‐substituted coralyne derivatives was examined by UV/VIS‐ and 1H‐NMR‐spectroscopy. Except for the dimethylamino‐substituted derivative, these cationic azoniaheterocyclic dyes undergo photocyclization that most likely proceeds through an initial E‐Z‐isomerization of the double bond. Subsequent oxidation of the intermediates under aerobic conditions gave the pyrrolo‐annelated quinolizinium derivatives as final products, thus providing a useful synthetic route to polycyclic azoniahetarene derivatives. The 6‐(4‐chlorophenyl)‐substituted pyrroloquinolizinium derivative was isolated on a preparative scale, and the investigation of its photophysical properties revealed significantly red‐shifted absorption (λabs = 465–480 nm) and emission bands (λfl = 550–562 nm) in comparison to the parent coralyne and the styryl‐substituted derivatives.

show abstract

Section: Resultsmentioning

confidence: 99%

Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives

Pithan

Ihmels

2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…Although the spectra of Figure 2 and Figure 3 did not offer sufficient evidence for the formation of aggregates in more polar methanol, reports of π-stacking in dimeric PQP + [ 48 , 51 ] and in BPDTQ + cations [ 50 ] led us to investigate the possible structures and electronic properties of the dimers of the 4a – c cations.…”

Section: Resultsmentioning

confidence: 99%

“…More recently, some of their derivatives such as 2-phenyl-benzo [8,9]quinolizino [4,5,6,7-fed]-phenanthridinylium tetrafluoroborate (PQPBF 4 ) have been shown to form columnar π-stacked aggregates in the solid phase [48]. Although such aggregation in acetonitrile has been disputed [49], spectral evidence for its formation in water has been obtained in our laboratories [50]. Thus, planar electron-deficient π-systems like PQP + or its dithienoquinolizium analog BPDTQ + should be good candidates for promising n-type semiconductors.…”

Section: Acceptormentioning

confidence: 99%

Alkylated Benzodithienoquinolizinium Salts as Possible Non-Fullerene Organic N-Type Semiconductors: An Experimental and Theoretical Study

et al. 2021

View full text Add to dashboard Cite

Three photobicyclized benzodithienoquinolizinium tetrafluoroborates (BPDTQBF4) were prepared and evaluated by UV–Vis and fluorescence spectral, electrochemical analysis, and by theoretical calculations as possible organic n-type semiconductors. Evaluation and comparison of their LUMO levels, HOMO-LUMO energy gaps as monomeric and π-stacked dimers with those of other materials, suggest their potential as organic n-type semiconductors. Calculations of their relative charge carrier mobilities confirmed this potential for one derivative with a long (C-14) alkyl chain appended to the polycyclic planar π-system.

show abstract

“…In contrast, its aqueous suspension showed broaden absorption bands with peaks at 339 and 447 nm. The lower intensity could be attributed to the formation of nanoparticles in water, which is known to be a common phenomenon [51–53] . To assign the absorption bands in the absorption spectra, time‐dependent DFT calculations were performed at the B3LYP/6‐311+G(2d,p) level of theory.…”

Section: Figurementioning

confidence: 99%

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Hamamoto

Kwek

et al. 2021

Angewandte Chemie

View full text Add to dashboard Cite

Polycyclic aromatic molecules are promising functional materials for a wide range of applications, especially in organic electronics. However, their largely hydrophobic nature has impeded further applications. As such, imparting high solubility/hydrophilicity to polycyclic aromatic molecules leads to a breakthrough in this research field. Herein, we report the synthesis of diazapentabenzocorannulenium, a cationic nitrogen‐embedded buckybowl bearing a central imidazolium core, by a bottom‐up strategy from polycyclic aromatic azomethine ylide. X‐ray crystallography analyses have revealed a bowl‐shaped molecular structure that is capable of forming charge‐segregated one‐dimensional columns by bowl‐in‐bowl packing. In addition to its fluorescence capabilities and high dispersibility in water, the molecule was found to selectively localize in the mitochondria of various tumor cells, showing potential as viable mitochondria‐selective fluorescent probes.

show abstract

Aggregation phenomena in photobicyclised pyridinium salts

Abstract: Absorption and emission spectra of PQPBF4 and BPDTQClO4 in water provide evidence, supported by theoretical calculations, of H-aggregation in this solvent.

Cited by 7 publications

References 17 publications

Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives

Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives

Alkylated Benzodithienoquinolizinium Salts as Possible Non-Fullerene Organic N-Type Semiconductors: An Experimental and Theoretical Study

Diazapentabenzocorannulenium: A Hydrophilic/Biophilic Cationic Buckybowl

Contact Info

Product

Resources

About