Please use this identifier to cite or link to this item:
Title: A p-quinodimethane-bridged porphyrin dimer
Authors: Zeng, W.
Ishida, M.
Lee, S.
Sung, Y.M.
Zeng, Z.
Ni, Y.
Chi, C. 
Kim, D.
Wu, J. 
Keywords: chromophores
polycyclic hydrocarbons
Issue Date: 2-Dec-2013
Citation: Zeng, W., Ishida, M., Lee, S., Sung, Y.M., Zeng, Z., Ni, Y., Chi, C., Kim, D., Wu, J. (2013-12-02). A p-quinodimethane-bridged porphyrin dimer. Chemistry - A European Journal 19 (49) : 16814-16824. ScholarBank@NUS Repository.
Abstract: A p-quinodimethane (p-QDM)-bridged porphyrin dimer 1 has been prepared for the first time. An unexpected Michael addition reaction took place when we attempted to synthesize compound 1 by reaction of the cross-conjugated keto-linked porphyrin dimers 8 a and 8 b with alkynyl/aryl Grignard reagents. Alternatively, compound 1 could be successfully prepared by intramolecular Friedel-Crafts alkylation of the diol-linked porphyrin dimer 14 with concomitant oxidation in air. Compound 1 shows intense one-photon absorption (OPA, λmax=955 nm, ε=45400 M-1 cm-1) and a large two-photon absorption (TPA) cross-section (σ(2) max=2080 GM at 1800 nm) in the near-infrared (NIR) region due to its extended π-conjugation and quinoidal character. It also exhibits a short singlet excited-state lifetime of 25 ps. The cyclic voltammogram of 1 displays multiple redox waves with a small electrochemical energy gap of 0.86 eV. The ground-state geometry, electronic structure, and optical properties of 1 have been further studied by density functional theory (DFT) calculations and compared with those of the keto-linked dimer 8 b. This research has revealed that incorporation of a p-QDM unit into the porphyrin framework had a significant impact on its optical and electronic properties, leading to a novel NIR OPA and TPA chromophore. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - A European Journal
ISSN: 09476539
DOI: 10.1002/chem.201302023
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.


checked on Jun 6, 2023


checked on Jun 6, 2023

Page view(s)

checked on Jun 8, 2023

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.