| Sažetak | Makrocikli su cikličke molekule koje se sastoje od najmanje 9 atoma u prstenu od kojih barem jedan mora biti
donor elektronskog para. Makrocikli su otkriveni sredinom 20. stoljeća i od tada predstavljaju važan dio raznih
polja istraživanja, kako u kemiji, tako i u biologiji i medicini. Makrocikličke Schiffove baze, zbog relativno
jednostavne primjene i sinteze, su sve više zastupljene u istraživanjima. Sastavni su dio makrocikličke kemije
koja je vrlo popularna i sve više se razvija. Tijekom nekoliko posljednjih desetljeća, znanstvenici su uspješno
proučavali različite vrste čvrstih materijala koji mogu selektivno vezati plinovite vrste. Među ovim materijalima
postoji veliki interes za makrocikle koji imaju poroznu strukturu, a u koju se mogu ugraditi molekule nekog
plina.
U ovome radu opisane su sinteze dviju novih makrocikličkih Schiffovih baza od benzaldehida i diamina. Svi
dobiveni produkti okarakterizirani su infracrvenom (FT-IR) spektroskopijom i termičkim metodama (TGADSC).
Rentgenskom strukturnom analizom utvrđeno je da prilikom slaganja molekula u kristal kod spoja 1,6,20,25 –
tetraaza-2,5:8,9:17,18:21,24:27,28:36,37 – heksabenzo-10,16,29,35 – tetraoksa – ciklooktatriakonta - 1,6,20,25
– tetraen (p-D1) nastaju šupljine. U nastale šupljine mogu se ugraditi različite plinovite vrste. Termičkom
analizom određen je udio pojedinih plinova koji se adsorbiraju u šupljikavu strukturu spoja. Analizom spojeva s
ugrađenim I2, NO2, Br2, CO2 i SO2 određeni su host/guest omjeri: I2 (1,5:1), NO2 (1:3), Br2 (2:1), CO2 (1:2,5) i
SO2 (2:1). Dobiveni rezultati su pokazali da prilikom adsorpcije plinova ne dolazi do promjene u molekulskoj
strukturi spoja.
Također, opisan je i metodički dio koji sadrži napisanu pripremu za nastavni sat za srednju školu na temu
„Onečišćenje i zaštita zraka“. Nastavni je sat osmišljen u vidu eksperimentalnog dokazivanja svojstava plinova
koji onečišćuju zrak (NOx, SO2 i CO2). Uz navedene pokuse, pripremljeni su pripadajući radni listići kako bi
učenici kemijskim zakonitostima objasnili pojave u pokusima. |
| Sažetak (engleski) | Macrocycles are cyclic molecules of at least 9 atoms in the ring, one of which is electron donor atom.
Macrocycles were discovered in mid 20th century and have been an important part of various fields of research,
in chemistry, biology and in medicine. Macrocyclic Schiff bases are lately more and more presented in scientific
studies due to the simplicity of their application and preparation. They are a part of macrocyclic chemistry that is
very popular and is being furthermore developed. In the past few decades, scientists have successfully studied
various types of solid materials that can selectively bind gaseous species. Among these materials, there is a great
interest in macrocycles that can form porous structures and subsequently bind gaseous species.
In this thesis, the synthesis and characterization of two new macrocyclic Schiff bases from benzaldehydes and
diamines are described. All products were characterized by infrared spectroscopy (FT-IR) and thermal methods
(TGA-DSC). The X-ray structural analysis of 1,6,20,25 – tetraaza - 2,5:8,9:17,18:21,24:27,28:36,37 –
heksabenzo-10,16,29,35 – tetraoksa – ciklooktatriakonta - 1,6,20,25 – tetraen (p-D1) showed a presence of a
nanometar sized voids in the crystal structure. As a result, gaseous species can be adsorbed into the voids. The
ratio of adsorbed gaseous species in hollow structure of a product was determined by thermal analysis. Analysis
of compound (p-D1) with adsorbed I2, NO2, Br2, CO2 and SO2 gave information on host/guest ratio: I2 (1,5:1),
NO2 (1:3), Br2 (2:1), CO2 (1:2,5) and SO2 (2:1). Obtained results have demonstrated that there is no change in
the molecular structure of compound during the adsorption of gaseous species.
This thesis also contains a part with teaching methods on high school level including printed preparation for
lesson on „Pollution and protection of air". The lesson is designed in form of an experimental demonstration of
properties of air pollutant gases (NOx, SO2 and CO2). Corresponding working papers are included in order for
students to explain the phenomena seen in given experiments. |
