Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/11012
Title: meso-Indolo[3,2-b]carbazolyl-Substituted Porphyrinoids: Synthesis, Characterization and Effect of the Number of Indolocarbazole Moieties on the Photophysical Properties
Authors: MAES, Wouter 
Ngo, Thien H.
Rong, Gu
Starukhin, Aleksander S.
Kruk, Mikalai M.
Dehaen, Wim
Issue Date: 2010
Publisher: WILEY-V C H VERLAG GMBH
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (13). p. 2576-2586
Abstract: meso-Indolocarbazolylporphyrins endowed with a different number of indolocarbazole units have been synthesized via condensation of an appropriately substituted monoformylated 5,11-dihydroindolo[3,2-b]carbazole precursor and mesityldipyrromethane. Under specific conditions, analogous meso-indolocarbazolylcorroles could also be prepared. The photophysical features of the novel luminiscent freebase and Zn-porphyrin derivatives were investigated. The introduction of indolocarbazole substituents results in progressive bathochromic shifts of the porphyrin absorbance and fluorescence bands due to the rising energy of the a2u orbital. The excitation energy is efficiently transferred from the meso-indolocarbazole units to the porphyrin macrocycle. An increased number of indolocarbazole moieties does not lead to porphyrin fluorescence quenching; on the contrary, a small increase of the fluorescence quantum yield is observed. The main route for excitation energy deactivation of all the studied porphyrins is intersystem S1→T1 crossing, with the intersystem crossing quantum yield, as determined by the photosensitized formation of singlet molecular oxygen, being as high as about 70% for the free-bases and more than 80% for the Zn complexes. The intersystem crossing quantum yield seems to be barely affected by meso-indolocarbazole substitution. A noticeable part of the excitation energy was found to deactivate through radiationless internal S1→S0 conversion.
Notes: [Maes, Wouter; Ngo, Thien H.; Rong, Gu; Dehaen, Wim] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium. [Maes, Wouter] Hasselt Univ, Inst Mat Res IMO, Res Grp Organ & Biopolymer Chem, B-3590 Diepenbeek, Belgium. [Starukhin, Aleksander S.; Kruk, Mikalai M.] Natl Acad Sci, BI Stepanov Inst Phys, Minsk 220072, Byelarus.
Keywords: Porphyrinoids; Nitrogen heterocycles; Photophysical properties; Luminescence; Molecular electronics; Excitation energy deactivation;Porphyrinoids; Nitrogen heterocycles; Photophysical properties; Luminescence; Molecular electronics; Excitation energy deactivation
Document URI: http://hdl.handle.net/1942/11012
ISSN: 1434-193X
e-ISSN: 1099-0690
DOI: 10.1002/ejoc.201000180
ISI #: 000277812100019
Category: A1
Type: Journal Contribution
Validations: ecoom 2011
Appears in Collections:Research publications

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