A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation
In the present work, we have explored the use of the triphenylmethyl group, a commonly used protecting group for primary alcohols as a gelling structural component in the design of molecular gelators. We synthesized a small library of triphenylmethyl derivatives of simple primary alcohols and studie...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.13.17 |
| _version_ | 1818617759069634560 |
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| author | Wangkhem P. Singh Rajkumar S. Singh |
| author_facet | Wangkhem P. Singh Rajkumar S. Singh |
| author_sort | Wangkhem P. Singh |
| collection | DOAJ |
| description | In the present work, we have explored the use of the triphenylmethyl group, a commonly used protecting group for primary alcohols as a gelling structural component in the design of molecular gelators. We synthesized a small library of triphenylmethyl derivatives of simple primary alcohols and studied their gelation properties in different solvents. Gelation efficiency for some of the derivatives was moderate to excellent with a minimum gelation concentration ranging between 0.5–4.0% w/v and a gel–sol transition temperature range of 31–75 °C. 1,8-Bis(trityloxy)octane, the ditrityl derivative of 1,8-octanediol was the most efficient organogelator. Detailed characterizations of the gel were carried out using scanning electron microscopy, FTIR spectroscopy, rheology and powder XRD techniques. This gel also showed a good absorption profile for a water soluble dye. Given the non-polar nature of this molecule, gel formation is likely to be mediated by hydrophobic interactions between the triphenylmethyl moieties and alkyl chains. Possible self-assembled packing arrangements in the gel state for 1,8-bis(trityloxy)octane and (hexadecyloxymethanetriyl)tribenzene are presented. Results from this study strongly indicate that triphenylmethyl group is a promising gelling structural unit which may be further exploited in the design of small molecule based gelators. |
| first_indexed | 2024-12-16T17:10:48Z |
| format | Article |
| id | doaj.art-10c6366fbd9d46698a450d1b22846e45 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T17:10:48Z |
| publishDate | 2017-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-10c6366fbd9d46698a450d1b22846e452022-12-21T22:23:24ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-01-0113113814910.3762/bjoc.13.171860-5397-13-17A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelationWangkhem P. Singh0Rajkumar S. Singh1Organic Materials Research Laboratory, Department of Basic Sciences & Social Sciences, North-Eastern Hill University, Shillong-793022, Meghalaya, IndiaOrganic Materials Research Laboratory, Department of Basic Sciences & Social Sciences, North-Eastern Hill University, Shillong-793022, Meghalaya, IndiaIn the present work, we have explored the use of the triphenylmethyl group, a commonly used protecting group for primary alcohols as a gelling structural component in the design of molecular gelators. We synthesized a small library of triphenylmethyl derivatives of simple primary alcohols and studied their gelation properties in different solvents. Gelation efficiency for some of the derivatives was moderate to excellent with a minimum gelation concentration ranging between 0.5–4.0% w/v and a gel–sol transition temperature range of 31–75 °C. 1,8-Bis(trityloxy)octane, the ditrityl derivative of 1,8-octanediol was the most efficient organogelator. Detailed characterizations of the gel were carried out using scanning electron microscopy, FTIR spectroscopy, rheology and powder XRD techniques. This gel also showed a good absorption profile for a water soluble dye. Given the non-polar nature of this molecule, gel formation is likely to be mediated by hydrophobic interactions between the triphenylmethyl moieties and alkyl chains. Possible self-assembled packing arrangements in the gel state for 1,8-bis(trityloxy)octane and (hexadecyloxymethanetriyl)tribenzene are presented. Results from this study strongly indicate that triphenylmethyl group is a promising gelling structural unit which may be further exploited in the design of small molecule based gelators.https://doi.org/10.3762/bjoc.13.17hydrophobic interactionsorganogelatorSEMtriphenylmethyl groupxerogel |
| spellingShingle | Wangkhem P. Singh Rajkumar S. Singh A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation Beilstein Journal of Organic Chemistry hydrophobic interactions organogelator SEM triphenylmethyl group xerogel |
| title | A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation |
| title_full | A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation |
| title_fullStr | A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation |
| title_full_unstemmed | A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation |
| title_short | A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation |
| title_sort | new class of organogelators based on triphenylmethyl derivatives of primary alcohols hydrophobic interactions alone can mediate gelation |
| topic | hydrophobic interactions organogelator SEM triphenylmethyl group xerogel |
| url | https://doi.org/10.3762/bjoc.13.17 |
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