Hierarchical self-assembly of water-soluble porphyrins

Synthetic Metals

Volumn 147, Issue 1-3, 2004, Pages 49-55

  Lauceri, Rosaria ^a   De Napoli, Massimo ^b   Mammana, Angela ^b   Nardis, Sara ^c   Romeo, Andrea ^d   Purrello, Roberta ^b  

^a CNR   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

^d UNIVERSITY OF MESSINA   (Italy)

Author keywords

Chiral memory; Self assembly; Water soluble porphyrins

Indexed keywords

AGGLOMERATION; AMINO ACIDS; ELECTROSTATICS; FLUORESCENCE; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SPECTROPHOTOMETERS; SUPRAMOLECULAR CHEMISTRY; THERMODYNAMICS;

CHIRAL MEMORY; PROTONATION; THERMODYNAMIC-KINETIC JUNCTION; WATER-SOLUBLE PORPHYRINS;

PORPHYRINS;

EID: 9944244464     PISSN: 03796779     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.synthmet.2004.05.031     Document Type: Conference Paper

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19. Meso-tetrakis(4-carboxyphenyl)porphyrin (H2TPPC) and meso-tetrakis(4- pyridyl)porphyrin (H2TPyP) have two different protonation sites: (i) the inner core nitrogen atoms and (ii) the carboxylic and pyridyl groups, respectively. However, no hierarchical self-aggregation has been observed in these cases. The deprotonation of the carboxylic acid groups of H2TPPC and the protonation of the pyridyl groups of H2TPyP increase their solubility in water. So, like H2TPPS, H2TPPC and H2TPyP have only one protonation step "useful" for aggregation.
20. The absence of the Soret band of the protonated form, can be attributed to two different phenomena: (i) a strong hypochromicity related to aggregation, or (ii) the protonation of the inner nitrogen atoms to very low pH values.
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23. The CD, intensity decreases by ≈30%, indicating that the smaller porphyrin aggregates (from dimers to roughly dodecamers) cross the membrane.