Supramolecular chirality in solvent-promoted aggregation of amphiphilic porphyrin derivatives: kinetic studies and comparison between solution behavior and solid-state morphology by AFM topography

Chemistry : a European Journal
Donato MontiRoberto Paolesse

Abstract

The solvent-promoted aggregation behavior of some amphiphilic porphyrin derivatives bearing chiral functionality in the form of a charged L-proline group has been investigated by UV/Vis, resonance light scattering, fluorescence and circular dichroism spectroscopy. The investigated macrocycles give rise to aggregates featuring supramolecular chirality with high ellipticity. Kinetic studies reveal peculiar differences in the fashion of aggregation, depending on the intimate nature of the chiral functionality, namely, cationic (nitrogen-quaternized L-proline, 3H(2)) or anionic (carboxylate residue, 6H(2)) group. Formation of anionic 6H(2) aggregates shows a diffusion-limited kinetic behavior. AFM topography studies show formation of tighter globular structures. On the other hand, the corresponding 3H(2) aggregates are formed by a cooperative, fractal-type decay, and appear as long-fibrous, looser structures. In the templated aggregation of 3H(2) over preformed 6H(2) aggregates, AFM images show formation of globular structures with reduced sizes, as a likely consequence of shorter interchromophore distances, due to favorable Coulombic interactions. The results obtained show an interesting parallelism between the solution behavior a...Continue Reading

References

Jan 1, 1995·Biophysical Journal·J C de PaulaR F Pasternack
Jun 27, 2000·Biophysical Journal·R F PasternackE J Gibbs
Oct 18, 2001·Journal of the American Chemical Society·L J PrinsD N Reinhoudt
Dec 13, 2001·Chemical Reviews·J J CornelissenN A Sommerdijk
Jan 5, 2002·Organic Letters·Vladimír KrálMichael Berger
Feb 7, 2002·Journal of the American Chemical Society·Rosaria LauceriRoberto Purrello
Aug 5, 1997·Chemical Reviews·Jennifer C. Ma, Dennis A. Dougherty
May 23, 2003·Angewandte Chemie·Teodor Silviu BalabanNicholas Vanthuyne
Apr 8, 2004·Chemical Communications : Chem Comm·Donato MontiGiovanna Mancini
Jul 21, 2004·Accounts of Chemical Research·Victor V BorovkovYoshihisa Inoue
Jul 29, 2004·Chemical Society Reviews·Miguel A Mateos-TimonedaDavid N Reinhoudt
Apr 20, 2005·Accounts of Chemical Research·D BradshawM J Rosseinsky
May 12, 2005·Chemical Communications : Chem Comm·Donato MontiRoberto Paolesse
May 26, 2005·Angewandte Chemie·Milan BalazRoberto Purrello
Jul 2, 2005·Chirality·Jing ZhangJames W Canary
Sep 22, 2005·Chemical Communications : Chem Comm·Eric Biron, Normand Voyer
Oct 6, 2005·Journal of the American Chemical Society·Jaap J D de JongBen L Feringa
May 4, 2006·Angewandte Chemie·Daniel FilippiniIngemar Lundström
Jun 24, 2006·Biosensors & Bioelectronics·Luisa S DolciRoberto Paolesse
Oct 6, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Penglei ChenMinghua Liu
Mar 7, 2007·Organic & Biomolecular Chemistry·Petr StepánekPavel Drasar
May 10, 2007·Journal of the American Chemical Society·Donato MontiRoberto Paolesse
Jun 8, 2007·Journal of the American Chemical Society·Angela MammanaRoberto Purrello
Jul 12, 2007·Chemical Communications : Chem Comm·Yusuke IshiiYuji Kubo
Jul 20, 2007·Chemical Communications : Chem Comm·Michael J InglesonMatthew J Rosseinsky
Apr 2, 2008·Chemical Communications : Chem Comm·Sankar MuniappanIsrael Goldberg
Oct 22, 2008·Organic & Biomolecular Chemistry·Imenne BouamaiedEugen Stulz
May 2, 2009·Journal of the American Chemical Society·Giovanna De LucaLuigi Monsù Scolaro
May 6, 2009·Angewandte Chemie·Hans-Jörg Schneider
May 7, 2009·Nanotechnology·Francesca DiniCorrado Di Natale
Oct 2, 2009·Journal of the American Chemical Society·Fernando BozoglianAntoni Llobet

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Citations

Oct 11, 2016·Organic & Biomolecular Chemistry·Francesca BiscagliaMarina Gobbo
Jun 13, 2018·Chemistry : a European Journal·Wenjie QianNúria Aliaga-Alcalde
Jul 14, 2010·Organic & Biomolecular Chemistry·Tom W AndersonG Dan Pantoş
Nov 20, 2010·Organic & Biomolecular Chemistry·Petr ŠtěpánekPavel Drašar
Feb 28, 2018·Physical Chemistry Chemical Physics : PCCP·Xiqian WangJianzhuang Jiang
Jan 8, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Federica SabuziPierluca Galloni
Oct 7, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Manuela StefanelliDonato Monti
Nov 19, 2020·International Journal of Molecular Sciences·Marco SavioliDonato Monti
Feb 2, 2012·The Journal of Physical Chemistry. B·Raquel TeixeiraSílvia M B Costa
Mar 6, 2019·ACS Applied Materials & Interfaces·Manuela StefanelliDonato Monti

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