Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments
The novel 18-membered macroheterocycle, namely, 11,22-dibromo-7,8,18,19-tetrahydrodibenzo[d,m]-[1,10, 2, 6,11,15]dioxatetraazacyclooctadecine-6,17(5H,16H)-dione, is shown to pack into a tubular supramolecular motif due to an extensive H-bonding, amide group dipoles electrostatic interactions, and π-...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2022-09-01
|
| Series: | Results in Materials |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2590048X22000504 |
| _version_ | 1811274660495491072 |
|---|---|
| author | Oleg V. Kulikov Victor Khrustalev Sergey Vodzinsky |
| author_facet | Oleg V. Kulikov Victor Khrustalev Sergey Vodzinsky |
| author_sort | Oleg V. Kulikov |
| collection | DOAJ |
| description | The novel 18-membered macroheterocycle, namely, 11,22-dibromo-7,8,18,19-tetrahydrodibenzo[d,m]-[1,10, 2, 6,11,15]dioxatetraazacyclooctadecine-6,17(5H,16H)-dione, is shown to pack into a tubular supramolecular motif due to an extensive H-bonding, amide group dipoles electrostatic interactions, and π-π stacking of their peripheral aromatic moieties. Noteworthy, both macrocyclic C=N–O segments adopted syn-configuration stabilized by intramolecular NH⋯O=C bonding. Apparently, molecules in the crystal form chains as a result of intermolecular H-bonding with a distance between adjacent macrocycles measured to be 9.2 Å. Overall, oxyimine-based macrocycles represent significant interest to the crystal engineering community as a convenient platform for making the elongated chain-like supramolecular motifs, and, possibly, tubular stacks or columnar alignments. |
| first_indexed | 2024-04-12T23:22:58Z |
| format | Article |
| id | doaj.art-bf18ca473cac4a73a9e47f0d847c0fe5 |
| institution | Directory Open Access Journal |
| issn | 2590-048X |
| language | English |
| last_indexed | 2024-04-12T23:22:58Z |
| publishDate | 2022-09-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Materials |
| spelling | doaj.art-bf18ca473cac4a73a9e47f0d847c0fe52022-12-22T03:12:29ZengElsevierResults in Materials2590-048X2022-09-0115100302Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segmentsOleg V. Kulikov0Victor Khrustalev1Sergey Vodzinsky2Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA; Huntsman Advanced Materials, The Woodlands, TX, 77381, USA; Corresponding author. Huntsman Advanced Materials, The Woodlands, TX, 77381, USA.N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences 119991 Moscow, Russian FederationI. I. Mechnikov Odessa National University, 65000, Odessa, UkraineThe novel 18-membered macroheterocycle, namely, 11,22-dibromo-7,8,18,19-tetrahydrodibenzo[d,m]-[1,10, 2, 6,11,15]dioxatetraazacyclooctadecine-6,17(5H,16H)-dione, is shown to pack into a tubular supramolecular motif due to an extensive H-bonding, amide group dipoles electrostatic interactions, and π-π stacking of their peripheral aromatic moieties. Noteworthy, both macrocyclic C=N–O segments adopted syn-configuration stabilized by intramolecular NH⋯O=C bonding. Apparently, molecules in the crystal form chains as a result of intermolecular H-bonding with a distance between adjacent macrocycles measured to be 9.2 Å. Overall, oxyimine-based macrocycles represent significant interest to the crystal engineering community as a convenient platform for making the elongated chain-like supramolecular motifs, and, possibly, tubular stacks or columnar alignments.http://www.sciencedirect.com/science/article/pii/S2590048X22000504 |
| spellingShingle | Oleg V. Kulikov Victor Khrustalev Sergey Vodzinsky Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments Results in Materials |
| title | Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments |
| title_full | Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments |
| title_fullStr | Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments |
| title_full_unstemmed | Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments |
| title_short | Tubular supramolecular motifs derived from 18-membered dibenzoN4O2 macrocycle incorporated syn-C=N–O segments |
| title_sort | tubular supramolecular motifs derived from 18 membered dibenzon4o2 macrocycle incorporated syn c n o segments |
| url | http://www.sciencedirect.com/science/article/pii/S2590048X22000504 |
| work_keys_str_mv | AT olegvkulikov tubularsupramolecularmotifsderivedfrom18membereddibenzon4o2macrocycleincorporatedsyncnosegments AT victorkhrustalev tubularsupramolecularmotifsderivedfrom18membereddibenzon4o2macrocycleincorporatedsyncnosegments AT sergeyvodzinsky tubularsupramolecularmotifsderivedfrom18membereddibenzon4o2macrocycleincorporatedsyncnosegments |