Issue 12, 2010
From the journal:

New Journal of Chemistry

J-aggregate formation in bis-(4-carboxyphenyl)porphyrins in water : pH and counterion dependence†

Vanda Vaz Serra,a   Suzana M. Andrade,b   Maria G. P. M. S. Neves,*a   José A. S. Cavaleiroa  and  Sílvia M. B. Costa*b  

* Corresponding authors

a Departamento de Química, Universidade de Aveiro, Campus Universitário de Santiago, 3810-193 Aveiro, Portugal
E-mail: gneves@ua.pt
Fax: +351 234 370084
Tel: +351 234 370710

b Centro de Química Estrutural, Complexo I; Instituto Superior Técnico, Av. Rovisco Pais, 1049-001 Lisbon, Portugal
E-mail: sbcosta@mail.ist.utl.pt
Fax: +351 21 8464455
Tel: +351 21 8419000

Abstract

The self aggregation behaviour of meso-tetraarylporphyrins containing two carboxyphenyl units in adjacent and opposite positions, respectively, 5,10-bis(4-carboxyphenyl)-15,20-diphenylporphyrin (DiCPP-adj) and 5,15-bis(4-carboxyphenyl)-10,20-diphenylporphyrin (DiCPP-opp), was investigated at different pH values. Ordered porphyrin architectures are obtained at pH = 0.8 and pH = 12 for both compounds studied, through an easy self assembly approach. The type of architecture and the extent of aggregation are related with the relative positions of the 4-carboxyphenyl groups attached to the porphyrin core and with the counterions present. The aggregates obtained exhibit spontaneous chirality, resonance light scattering, short fluorescence lifetimes and low fluorescence quantum yields. The data gives evidence that at pH = 0.8 with NO3− the preferred aggregation is more favoured for DiCPP-adj than for DiCPP-opp, whereas at pH = 12 the aggregate of DiCPP-opp is induced by Na+ and Li+ cations and stabilized by hydrophobic interactions. Deposition of aqueous solutions at key pHs on glass surfaces enables the detection of circular and ring aggregates viewed by fluorescence lifetime imaging microscopy (FLIM) with dimensions of a few micrometres.

Graphical abstract: J-aggregate formation in bis-(4-carboxyphenyl)porphyrins in water : pH and counterion dependence

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C0NJ00201A
Article type
Paper
Submitted
16 Mar 2010
Accepted
09 Jun 2010
First published
26 Aug 2010

New J. Chem., 2010,34, 2757-2765

Permissions

Request permissions

J-aggregate formation in bis-(4-carboxyphenyl)porphyrins in water : pH and counterion dependence

V. V. Serra, S. M. Andrade, M. G. P. M. S. Neves, J. A. S. Cavaleiro and S. M. B. Costa, New J. Chem., 2010, 34, 2757 DOI: 10.1039/C0NJ00201A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements