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Author:Wahlström, Ronny
Title:Reversibelt syrebindande organometalliska komplex
Reversibly oxygen binding organometallic complexes
Reversiibelisti happea sitovat organometallikompleksit
Publication type:Master's thesis
Publication year:2009
Pages:ix + 114 (+20)      Language:   swe
Department/School:Kemian laitos
Main subject:Orgaaninen kemia   (Kem-4)
Supervisor:Koskinen, Ari
Instructor:Pitkänen, Pauliina
OEVS:
Electronic archive copy is available via Aalto Thesis Database.
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Location:P1 Ark TKK  3856   | Archive
Keywords:phthahocyanine
phthalonitrile
oxygen transport
porphyrin
metal complex
ftalosyaniini
ftalonitriili
hapen kuljetus
porfyriini
metallikompleksi
ftalocyanin
ftalonitril
syretransport
porfyrin
metallkomplex
Abstract (eng): To porphyrins structurally related organometallic complexes, which bind oxygen reversibly, have been used in oxygen enriching processes either as actively oxygen binding groups in oxygen enriching membranes, or as mobile oxygen carriers in solution.
The complexes of interest for this work are metalloporphyrins, -porphyrazines and -phthalocyanines.

In the literature survey biological oxygen enriching systems are briefly discussed, as well as artificial systems where oxygen is enriched by mobile oxygen carriers or by oxygen enriching membranes.
Metal complexes of porphyrins, porphyrazines and phthalocyanines are dealt with as potential oxygen carriers.
Their synthesis, and especially their solubility and aggregation is discussed, since they are important properties to be tuned in order to maximize the oxygen transport capability in solution.
The metallophthalocyanines were found to be the easiest to synthesize and the work is concentrated on them.
The synthesis of metallophthalocyanines as well as methods for introducing substituents on them is reviewed in detail.
Cobaltphthalocyanines have been found to be among the most suitable for oxygen transport, but the presence of the ferromagnetic Co(II) ion makes NMR analysis impossible.
Therefore, the analysis and caracterization of phthalocyanines are discussed too.

In the experimental part, the microwave assisted synthesis of a tetra-tert-butyl and a tetrafluoro substituted cobaltphthalocyanine is explored with two different methods, but with poor product quality.
In the following experiments two water soluble cobalt-phthalocyanines are synthesized successfully, and they are characterized by IR, UV-Vis and mass spectroscopy.
The analysis clearly indicates that the complexes dimerize in water, but exist as monomers in methanol solution.
The water solubility is due to charged substituents: the first phthalocyanine is substituted with four by methylene quaternized pyridyloxy groups; the second phthalocyanine is substituted with four isophthalate phenoxy groups.
The phthalocyanines were synthesized in refluxing pentanol with basic catalysis out of the corresponding phthalonitrile and metal salt.
The phthalonitrile was formed by nucleophilic aromatic nitro replacement.
Abstract (swe): Reversibelt syrebindande organometalliska komplex, som är strukturellt besläktade med porfyriner, har använts i syreanrikande processer, antingen som aktivt syrebindande grupp på syreanrikande membran eller som mobila syretransportörer i lösning.
De komplex, vilka är av intresse för detta diplomarbete, är av tre typer: metallporfyriner, -porfiraziner och -ftalocyaniner, vilka alla tre är kända för sina syrebindande egenskaper.

I litteraturdelen granskas kort syretransport i biologiska system, samt i artificiella system där syre anrikas via mobila syretransportörer eller syreanrikande membran.
Som potentiella syretransportörer behandlas metallkomplex av porfyriner, porfyraziner och ftalocyaniner, i Ijuset av deras syntetik och egenskaper, med särskild vikt på löslighet och aggregering, eftersom dessa egenskaper är viktiga att kontrollera för att uppnå maximal syretransportförmåga i lösning.
Metallftalocyaninerna konstaterades vara lättast syntetiserbara och arbetet koncentrerades på dem.
Metallftalocyaninernas syntetik redogörs noggrannt och metodologin för införandet av olika substituenter, som påverkar deras egenskaper, granskas i detalj.
Koboltftalocyaniner har konstaterats vara lämpiiga för syretransport, men närvaron av den ferromagnetiska Co(II)jonen omöjliggör NMR-analys av komplexen, varför ftalocyaninernas analytik också behandlats kort.

I den experimentella delen utförs inledningsvis mikrovågsaccelererad syntes av tetra-tert-butyl- och tetrafluorosubstituerad koboltftalocyanin mcd två olika metoder, men produkterna som erhölls var inte av önskvärd kvalitet.
I vidare experiment syntetiserades två vattenlösliga koboltftalocyaniner med framgång, och karakteriseras med hjälp av IR, UV-Vis, och masspektroskopi.
Analysen visar att bägge komplexen bildar dimerer i vattenlösning, men löser sig som monomerer i metanol.
Vattenlösligheten beror på närvaron av laddade substituenter, i det ena fallet fyra med metylgrupp kvaterniserade pyriclyloxisubstituenter, i det andra fallet fyra iso-ftalatfenoxisubstituenter.
Ftalocyaninerna syntetiserades i kokande arnylalkohollösning mcd basisk katalysator ur korresponderande ftalonitrilderivat och koboltklorid; ftalonitrilderivatet tiliverkades via nukleofil aromatisk förskjutning.
ED:2009-10-12
INSSI record number: 38458
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