Sinteza 1,4-bis(nitrometil)benzena za pripravo poli(arilen nitro-vinilena) s Henry-jevo kondenzacijo : magistrsko delo

Patik, Eva

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Title:	Sinteza 1,4-bis(nitrometil)benzena za pripravo poli(arilen nitro-vinilena) s Henry-jevo kondenzacijo : magistrsko delo
Authors:	ID Patik, Eva (Author) ID Kovačič, Sebastijan (Mentor) More about this mentor...
Files:	MAG_Patik_Eva_2026.pdf (6,36 MB) MD5: BB885EA275DEAAD5C52187411F1787AC
Language:	Slovenian
Work type:	Master's thesis/paper
Typology:	2.09 - Master's Thesis
Organization:	FKKT - Faculty of Chemistry and Chemical Engineering
Abstract:	Konjugirani porozni polimeri CPP lahko zaradi svoje porozne strukture z obsežnim π-konjugiranim sistemom izkazujejo polprevodniške in fotokatalitske lastnosti. Magistrska naloga se osredotoča na sintezo takšnega materiala s Henry-jevo kondenzacijsko reakcijo, pri čemer je potrebna predhodna sinteza komercialno nedostopnega reaktanta 1,4-bis(nitrometil)benzena po treh sinteznih poteh iz 1,4-bis(bromometil)benzena ali tereftalaldehida. Med raziskavo smo ugotovili, da je oksidacija 1,4-bis(aminometil)benzena do 1,4-bis(nitrometil)benzena močno omejena zaradi prednostne oksidacije benzilnega metilenskega mesta. Zato smo razvili alternativni pristop, ki temelji na kvarternizaciji diamina in njegovi nadaljnji uporabi v polikondenzaciji. Predstavljene so sintezne reakcije, ki vodijo do želenega nitroalkana in vmesnih produktov, njihova izolacija ter karakterizacija z uporabo 1H ali 13C NMR ter ATR-FTIR spektroskopij. Alternativni pristop s kvarternizacijo diamina nakazuje možnost priprave sorodnih konjugiranih sistemov, vendar bi bila za popolno strukturno potrditev in ovrednotenje lastnosti potrebna dodatna karakterizacija. Rezultati 13C CP MAS NMR potrjujejo, da smo z dodatkom piperidina v reakcijsko zmes 1,4-bis(nitrometil)benzena in tereftalaldehida uspešno sintetizirali poli(arilen nitro-vinilen), meritve UV-Vis DRS pa nakazujejo na nastanek obsežnega π-konjugiranega skeleta ustvarjenega materiala s potencialnimi polprevodniškimi lastnostmi.
Keywords:	konjugirani porozni polimeri, Henry-jeva kondenzacijska reakcija, Staudingerjeva redukcija, 1, 4-bis(nitrometil)benzen, tereftalaldehid
Place of publishing:	Maribor
Place of performance:	Maribor
Publisher:	[E. Patik]
Year of publishing:	2026
Number of pages:	1 spletni vir (1 datoteka PDF (XI, 79 str.))
PID:	20.500.12556/DKUM-97454
UDC:	547.53.057:66.095.3(043.2)
COBISS.SI-ID:	273716483
Publication date in DKUM:	26.03.2026
Views:	133
Downloads:	85
Metadata:
Categories:	KTFMB - FKKT
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Licences

License:	CC BY-NC-ND 4.0, Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International

Link:	http://creativecommons.org/licenses/by-nc-nd/4.0/
Description:	The most restrictive Creative Commons license. This only allows people to download and share the work for no commercial gain and for no other purposes.
Licensing start date:	10.03.2026

Secondary language

Language:	English
Title:	Synthesis of 1,4-bis(nitromethyl)benzene for the preparation of poly(arylene nitro-vinylene) by Henry condensation
Abstract:	Conjugated porous polymers CPPs can exhibit semiconducting and photocatalytic properties due to their porous structure and extensive π-conjugated system. This master's thesis focuses on the preparation of such a material via Henry condensation, with prior synthesis of the commercially unavailable reactant 1,4-bis(nitromethyl)benzene from either 1,4-bis(bromomethyl)benzene or terephthalaldehyde, using three synthetic routes. During our research, we found that oxidation of 1,4-bis(aminomethyl)benzene to 1,4-bis(nitromethyl)benzene is severely limited due to preferential oxidation at the benzyl methylene site. Therefore, we developed an alternative approach based on quaternisation of the diamine and its subsequent use in polycondensation. We have presented the synthesis reactions leading to the desired product and its intermediates, as well as their isolation and characterisation using 1H or 13C NMR and ATR-FTIR. The alternative approach involves the synthesis of poly(arylene quaternary amine-vinylene), demonstrating the usefulness of quaternised diamine as a monomer for preparing of related conjugated polymers. The results of 13C CP MAS NMR confirm that, by adding piperidine to the reaction mixture of 1,4-bis(nitromethyl)benzene and terephthalaldehyde, we have successfully synthesised poly(arylene nitro-vinylene), while UV-Vis DRS measurements indicate its potential semiconducting properties with an extensive π-conjugated framework.
Keywords:	conjugated porous polymers, Henry condensation reaction, Staudinger reduction, 1, 4-bis(nitromethyl)benzene, terephthalaldehyde

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