A first archetype of boron dipyrromethene-phthalocyanine pentad dye: design, synthesis, and photophysical and photochemical properties

A novel type of phthalocyanine pentad containing four boron dipyrromethene ( BODIPY ) units at peripheral positions of the phthalocyanine framework has been designed and synthesized for the first time. The Sonogashira coupling reaction between 4,4′-difluoro-8-(4-ethynyl)-phenyl-1,3,5,7-tetramethyl-4...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2014-05, Vol.43 (2), p.7561-7569
Main Authors: Göl, Cem, Malkoç, Mustafa, Ye ilot, Serkan, Durmu, Mahmut
Format: Article
Language:English
Subjects:
Boron
Boron Compounds - chemical synthesis
Boron Compounds - chemistry
Chemistry Techniques, Synthetic
Coloring Agents - chemical synthesis
Coloring Agents - chemistry
Design engineering
Drug Design
Dyes
Energy Transfer
Indoles - chemistry
Joining
Photochemical
Photolysis
Photosensitizing Agents - chemical synthesis
Photosensitizing Agents - chemistry
Singlet Oxygen - chemistry
Synthesis
Tetrahydrofuran
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Summary:A novel type of phthalocyanine pentad containing four boron dipyrromethene ( BODIPY ) units at peripheral positions of the phthalocyanine framework has been designed and synthesized for the first time. The Sonogashira coupling reaction between 4,4′-difluoro-8-(4-ethynyl)-phenyl-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene ( Ethynyl-BODIPY ) and 2(3),9(10),16(17),23(24)-tetrakis(iodo) zinc( ii ) phthalocyanine ( Iodo-Pc ) has been used for the synthesis of the target compound. The BODIPY-phthalocyanine pentad dye ( BODIPY-Pc ) has been fully characterized by 1 H NMR, MALDI-TOF mass, FT-IR and UV-Vis spectroscopic techniques and elemental analysis as well. The photoinduced energy transfer process for this dye system was explored in tetrahydrofuran solution. The singlet oxygen generation capability and photodegradation behaviours of this BODIPY-Pc pentad dye were also investigated in DMSO for the determination of the usability of this new type of dye system as a photosensitizer in PDT applications. A novel type of symmetrical tetra-boron dipyrromethene (BODIPY) substituted zinc( ii ) phthalocyanine (Pc) pentad dye (BODIPY-Pc) has been designed and synthesized which exhibits panchromatic behaviour, predominant energy transfer process and high singlet oxygen generation.
ISSN:1477-9226
1477-9234
DOI:10.1039/c4dt00406j