Proiect PN-II-RU-TE-2014-4-0727:   Project timespan   Project team   Abstract   Project objectives   Budget   Results  

Title:

Funding authority: National Research Council of Romania
Contract number: 231/01.10.2015

Project manager: Conf. Dr. Niculina D. Hădade ResearcherID: F-9489-2011

Team:
  1. Dr. Andreea Diac
  2. Lidia Pop
  3. Gabrian Levi Mihai
  4. Virlan (cas. Mate) Nadejda
Project timespan
2015 -- 2017

Abstract
Development of 3D molecular organic cages with large internal cavities has emerged as an important research area of supramolecular chemistry mainly due to their usefulness as host molecules with enhanced guest binding properties, nanoporous materials with well-defined pores and large internal surface area as well as sensors. Among the most important challenges in the achievement of such molecules we can mention their laborious multi-step synthesis and the difficulty to preserve the integrity of the internal cavity in the solid state. Herein, we propose the design and synthesis of rigid and semi-flexible naphthalene diimide-based 3D cage molecules with trigonal prismatic, square prismatic and hexagonal prismatic geometries as proper candidates to obtain materials with improved gas absorption capacities as well as selective receptors for organic small molecules. Moreover, considering the electronic and spectroscopic properties of the naphthalene diimide units, the proposed structures meet the requirements of molecular sensors. One-pot or sequential dynamic synthesis using imine exchange and/or alkynes metathesis reversible reactions in a classical dynamic covalent chemistry (DCC) process will be used in order to achieve the target structures. In addition, taking advantage of the orthogonality between the imine formation and alkynes metathesis, an Orthogonal Dynamic Covalent Chemistry (ODCC) strategy shall also be used for the synthesis of the cage compounds.

Budget

Budget chapter (expenses) 2015 (lei) 2016 (lei) 2017 (lei) Total
1 Salaries 29.000 135.200 145.904 299.904
2 Inventory 5.869,57 68.759,65 88.727,64 163.356,86
3 Mobility 0 5.555,13 9.444,87 15.000
4 Overhead 10.130,43 31.427,22 30.181,49 71.739,14
5 Total 45.000 240.942 264.058 550.000

Results
  • Synthesis and characterization of the 3D cages intermediate: ethinyl-, formyl- and amino-decorated corner units as well as ethynyl and amino-ended linkers.
  • Synthesis and characterization of naphthalene diimide based macrocycles.
  • Development of a new method for selective hydration of activated aromatic alkynes using a Mo(VI) catalyst.
Articles
  • Naphtalene diimide motif in macrocycles and interlocked molecules: synthesis and applications, Andreea Diac, Mihaela Matache, Niculina D. Hădade; to be submitted in December 2016 to Organic Chemistry Frontiers.
Attended conferences
  1. Niculina D. Hădade - A short journey through the geometrical and thermodynamical space of supramolecular and Dynamic Adaptive Chemistry Diaspora în Cercetarea Științifică și Învățământul Superior din România, 25-28 April 2016, Timișoara, Romania (ORAL PRESENTATION).
  2. Andreea P. Diac, Alexandra Bogdan, Niculina D. Hădade, Ion Grosu - On the eve of the synthesis of a new photochemical molecular machine with conformational versatility, 27th European Colloquium on Heterocyclic Chemistry, 3-6 July, Amsterdam, Netherlands (POSTER).
  3. Levi Gabrian, Niculina D. Hădade, Anamaria Terec, Ion Grosu - An Approach Towards Obtaining some New Molecular Cages Containing Phenanthroline Derivatives as Side Arms, A XXXIV-a Conferinta Nationala de Chimie , 04-07 Octombrie 2016, Calimanesti-Caciulata (POSTER).
  4. Lidia Pop, Niculina D. Hădade, Ion Grosu - Charge-Assisted Hydrogen Bonding Self-Assembly of Bis-Amidine Complexes, A XXXIV-a Conferinta Nationala de Chimie , 04-07 Octombrie 2016, Calimanesti-Caciulata. (ORAL PRESENTATION)
BSc Thesis
  • Sinteza și caracterizarea unor derivați ai naftalendiimidei: intermediari cheie în obținerea de cuști 3D rigide – Maria Cristina Lupas
For information about unpublished results contact Dr. Niculina D. Hădade at nbogdan (at) chem.ubbcluj.ro.