Yeni Esnek Ditiya-alkil Köprülü Homo-dimerik Metalsiz ve Metalli ftalosyaninler

Year 2017, Issue: 1, 31 - 35, 31.12.2017

Rıza Bayrak , İsmail Değirmencioğlu

Abstract

Bu çalışmada,  homo dimerik metal içermeyen ve
metaloftalosiyaninlerin organik çözücülerde spektroskopik özelliklerinin
sentezi, karakterizasyonu ve araştırılması gerçekleştirilmiştir.
Ftalosiyaninlerin sentezi için başlangıç ​​bileşiği olarak seçilmiş diftalonitril
türevi, 4-nitroftalonitril ve bileşik l'in kuru dimetilformamid / potasyum
karbonat içinde reaksiyonu ile hazırlandı. 1:6.15 oranında ftalonitril ile
substitue diftalonitrilin siklotetramerasizasyonu, beklenen homo-dimerik metal
içermeyen ftalosiyanini ve Zn(II), Ni(II), Co(II) ve Cu(II) metal tuzları ile
tetramerizasyonu da, binükleer Zn-, Ni-, Co- and Cu- ftalosyaninleri oluşturdu. Tüm bu reaksiyonlar,
DMAE/1,8-diazabicyclo [5.4.0] undec-7-ene sisteminde gerçekleştirildi. Ürünler, kristallendirme ve silika jel kolon
kromatografisi ile saflaştırıldı. Yeni hazırlanan bileşikler,  IR, 1H / 13C-NMR, MS ve
UV-Vis spektroskopisinin kombinasyonu ile karakterize edildi. Ayrıca, tüm yeni
ftalosiyaninlerin agregasyon davranışları da araştırılmıştır. Metal içermeyen
metalli-ftalosiyaninlerin agregasyon özellikleri kloroformda araştırılmıştır.
Dimerik metal içermeyen metalli-ftalosiyaninler kloroformda 4x10-6-16x10-6
mol/L konsantrasyon aralığında agregasyon göstermemiştir. Ayrıca kloroform, N,N-dimetil
formamid, dimetilsülfoksit, piridin ve tetrahidrofuranda Co-ftalosiyanin
molekülünün agregasyon özellikleri araştırılmıştır. Co-ftalosiyanin molekülü,
1x10-5 mol/L konsantrasyonda belirtilen çözücülerde monomerik
davranış göstermiştir.

Keywords

agregasyon, dimerik ftalosiyanin, ftalosiyanin, sentez, spektroskopi

Novel Flexible Dithia-alkyl Bridged Homo-dimeric Metal-free and Metallophthalocyanines

Abstract

In
this study, synthesis, characterization and investigation of spectroscopic
properties in organic solvents of homo dimeric metal free and
metallophthalocyanines have been carried out. The substituted di-phthalonitrile
derivative as a starting material for the synthesis of phthalocyanines was
prepared by the reaction of 4-nitrophthalonitrile and compound 1 in dry dimethylformamide/potassium
carbonate. The cyclotetramerization of substituted diphthalonitrile derivative with phthalonitrile in 1:6.15 ratio
gave the expected homo-dimeric metal-free phthalocyanine and with metal salts
of Zn(II), Ni(II), Co(II) and Cu(II) gave binuclear Zn-, Ni-, Co- and
Cu-phthalocyanines, respectively, in
dimethyl aminoethanol/1,8-diazabicyclo [5.4.0] undec-7-ene system. The
products were purified by crystallization and silica gel column chromatography.
The newly prepared compounds were characterized by a combination of IR, 1H
/ 13C-NMR, MS and UV-Vis spectroscopy. In addition, aggregation
behaviors of all novel phthalocyanines were investigated. Aggregation properties
of the metal free and metallophthalocyanines have been investigated in
chloroform. Dimeric metal free and metallophthalocyanines did not show
aggregation in chloroform at 4x10-6–16x10-6 mol/L concentration
range. Furthermore, aggregation properties of Co- phthalocyanine have been investigated
in chloroform, N,N–dimethyl formamide, dimethylsulfoxide, pyridine and
tetrahydrofurane. Co-phthalocyanine complex showed monomeric behavior in
mentioned solvents at 1x10-5 mol/L concentration.

Keywords

Aggregation, dimeric phthalocyanine, phthalocyanine, synthesis, spectroscopy

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