Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

Abstract

This study introduces new triazole-linked host compounds, which have been synthesized from 7,8-dioxa-bisnaphthalene and 7,8-dioxa[6]helicenes. These compounds have different cavities depending on being ‘v’-shaped or helicene structures. The dimeric structure of 7,8-dioxa-bisnaphthalene has also been obtained and crystal structure analysis confirmed that it contains an unusual seven-membered dihydrooxepine ring. All synthesized compounds can act as molecular tweezers for organic molecules and also metal ions.

The Synthesis of New Triazole‐Linked Supramolecules Based on Bis‐[1,3]‐Naphthodioxocines

“…2,3-DNDO derivatives according to the procedures given in Scheme 1. Compounds 10 and 11 were obtained as reported previously [19] from malonaldehyde dimethyl acetal and 2,3-and 2,7-dihydroxynaphthalene respectively. Then, they reacted with propargyl bromide to afford propargyl ethers 12 and 13.…”

“…Compounds 16 and 17 were obtained from dibromide derivatives with using sodium azide in DMF as reported earlier. [19] For the azide-alkyne cycloaddition reaction, we firstly tried the reaction between compounds 13 and 17 for the synthesis of product (compound 8) with using 0.1 eq. CuBr as catalyst without the ligand.…”

“…[7][8][9][10] In the discipline of host-guest chemistry, there are various molecular scaffolds serving as host molecules in the above mentioned areas, such as cyclodextrines, [11] calixarenes, [12][13] porphyrines, [13][14][15] cucurbiturils, [16] and helical molecules. [17][18][19] In recent years, 1,3-dioxanaphthalen derivatives -found in nature showing a number of biological activities [20][21] -has been added to this list. Especially, 8,16-methano-16H-dinaphtho [2,1-d: 1',2'g] [1,3]dioxocine (DNDO) derivatives 1 has found applications as molecular tweezers due to their electron rich, deep, and wide hydrophobic cavities.…”

“…[24] Gejji and coworkers reported the encapsulation of neutral DABCO using bis-thiourea/urea functionalized DNDO 4 as molecular tube. [25] In our previous study, we synthesized new potential molecular tweezers, bis-triazolyl DNDO derivative 5 and tetra triazolyl-7a,14c-dihydro-naphtho[2,1b][1',2';4,5]furo [3,2]furan derivative [19] (DNFF) 6 (Figure 1). They have different inner cavity for complexation with metal ions or neutral molecules.…”

The synthesis and crystal structure of pH-sensitive fluorescent pyrene-based double aza- and diaza[4]helicenes

“…in these molecules helps in fine tuning their optoelectronic properties. 10 One more promising modification of the helicene structure is condensation with different polycyclic aromatic molecules, which allows extending the π-system and improving useful characteristics. In particular, reports in the last few decades have highlighted carbo- and heterohelicenes, incorporating the pyrene fragment, as a very attractive class of compounds.…”