Proton-coupled self-assembly of a porphyrin-naphthalenediimide dyad

Siyu Tu; Se Hye Kim; Jojo Joseph; David A Modarelli; Jon R Parquette

doi:10.1002/cphc.201300023

Proton-coupled self-assembly of a porphyrin-naphthalenediimide dyad

Chemphyschem. 2013 Jun 3;14(8):1609-17. doi: 10.1002/cphc.201300023. Epub 2013 Apr 5.

Authors

Siyu Tu¹, Se Hye Kim, Jojo Joseph, David A Modarelli, Jon R Parquette

Affiliation

¹ Department of Chemistry, The Ohio State University, 100W. 18th. Avenue, Columbus, Ohio 43210, USA.

PMID: 23564748
DOI: 10.1002/cphc.201300023

Abstract

The construction of an n-p heterojunction through the self-assembly of a dyad based on tetraphenylporphyrin (TPP) and 1,4,5,8-naphthalenedimide (NDI) (1) is described. Proton transfer from the lysine head group of 1 to the porphyrin ring occurs concomitantly with self-assembly into 1D nanorods in CHCl3. TEM and AFM studies showed that the nanorods are formed by the lateral and vertical fusion of multilameller vesicles into networks and hollow ribbons, respectively. These intermediate structures transitioned to nanorods over the course of 4-6 days. Time-resolved spectroscopy revealed that photoinduced charge separation occurs with rate constants that depend on the nature of the aggregation.