2016
DOI: 10.1016/j.poly.2016.03.019
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Microwave-assisted synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines bearing tetra terminal-alkynyl functionalities and click approach

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Cited by 27 publications
(10 citation statements)
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“…Especially phthalocyanines (Pc), second- and third-generation photosensitizers, have a lot of advantages in PDT applications because of their superior absorption in the phototherapeutic window . In addition, their chemical structure is easily modified by replacing central metals and adding peripheral and nonperipheral substituents. These changes allow to easily adjust chemical and physical properties, pharmacokinetics, and biodistributions of phthalocyanines …”
Section: Introductionmentioning
confidence: 99%
“…Especially phthalocyanines (Pc), second- and third-generation photosensitizers, have a lot of advantages in PDT applications because of their superior absorption in the phototherapeutic window . In addition, their chemical structure is easily modified by replacing central metals and adding peripheral and nonperipheral substituents. These changes allow to easily adjust chemical and physical properties, pharmacokinetics, and biodistributions of phthalocyanines …”
Section: Introductionmentioning
confidence: 99%
“…Nevertheless, it still often requires an organic base, commonly 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), to catalyze the reagent tetramerization and reaction media such as alkyl alcohols (pentanol, hexanol), dimethylaminoethanol (DMAE) nitrobenzene, chlorobenzene, quinoline and α-chloronaphthalene [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ], most of which are non-environmentally friendly. Given their extreme technological importance, many unconventional synthetic approaches have been studied and developed in parallel with their applications to increase their yields and sustainability while reducing their production cost, such as (i) microwave-assisted [ 22 ] and UV-assisted [ 23 , 24 ] processes, which are usually much faster and cleaner than their “standard” counterparts but requiring specific instrumentation and lacking scalability, and (ii) room-temperature reactions promoted by strong organic bases such as lithium diisopropylamide (LDA) [ 25 ] and pre-formed lithium alcoholate solutions [ 26 ]. With a view to increase the sustainability of the phthalocyanine synthesis on the lab scale, we systematically studied the effect of solvent and base replacement on the yield and cost of the macrocyclization reaction of phthalonitrile and 4- tert -butylphthalonitile templated by three first-transition metal ions: Co(II), Cu(II) and Zn(II).…”
Section: Introductionmentioning
confidence: 99%
“…UV-Vis spectroscopy is thought to be the basic method to verify the formation of phthalocyanines. The phthalocyanine compounds show two main electronic transitions named as Q band (600-700 nm in the visible region), assigned to the - * transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) of the Pc ring, and B band (300-350 nm in the UV region), resulting from the deeper - * transitions [20][21][22]. The UV spectra of the metallophthalocyanines ( -) display intense Q band at 675 nm for , 663 nm for , 671 nm for , Journal of Chemistry and 675 nm for in THF.…”
Section: Synthesis and Characterization Ofmentioning
confidence: 99%