Göl Cem, Malkoç Mustafa, Yeşilot Serkan, Durmuş Mahmut
Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, 41400, Gebze, Kocaeli, Turkey.
Dalton Trans. 2014 May 28;43(20):7561-9. doi: 10.1039/c4dt00406j.
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.
首次设计并合成了一种新型的酞菁五元体，其在酞菁骨架的外围位置含有四个硼二吡咯亚甲基（BODIPY）单元。利用4,4'-二氟-8-(4-乙炔基)-苯基-1,3,5,7-四甲基-4-硼-3a,4a-二氮杂-s-茚（乙炔基-BODIPY）与2(3),9(10),16(17),23(24)-四（碘）锌（II）酞菁（碘代-Pc）之间的Sonogashira偶联反应来合成目标化合物。通过（1）H NMR、基质辅助激光解吸电离飞行时间质谱（MALDI-TOF mass）、傅里叶变换红外光谱（FT-IR）和紫外可见光谱技术以及元素分析对BODIPY-酞菁五元体染料（BODIPY-Pc）进行了全面表征。在四氢呋喃溶液中探索了该染料体系的光致能量转移过程。还在二甲基亚砜中研究了这种BODIPY-Pc五元体染料的单线态氧生成能力和光降解行为，以确定这种新型染料体系作为光动力疗法（PDT）应用中的光敏剂的可用性。
