التفاصيل البيبلوغرافية
| العنوان: |
Enhanced ion binding by the benzocrown receptor and a carbonyl of the aminonaphthalimide fluorophore in water-soluble logic gates. |
| المؤلفون: |
Diacono A; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Aquilina MC; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Calleja A; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Agius G; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Gauci G; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Szaciłowski K; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt., Magri DC; Department of Chemistry, Faculty of Science, University of Malta, Msida, MSD 2080, Malta. david.magri@um.edu.mt. |
| المصدر: |
Organic & biomolecular chemistry [Org Biomol Chem] 2020 Jul 01; Vol. 18 (25), pp. 4773-4782. |
| نوع المنشور: |
Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: |
English |
| بيانات الدورية: |
Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Print Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: PubMed not MEDLINE; MEDLINE |
| أسماء مطبوعة: |
Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003- |
| مستخلص: |
Two fluorescent logic gates 1 and 2 were designed and synthesised with a 'receptor1-spacer1-fluorophore-spacer2-receptor2' format. The molecules comprise of an aminonaphthalimide fluorophore, methylpiperazine and either benzo-15-crown-5 or benzo-18-crown-6. Model 3, with a weakly binding 3,4-dimethoxyphenyl moiety, was also synthesised. The compounds were studied both in 1 : 1 (v/v) methanol/water and water by UV-visible absorption and steady-state fluorescence spectroscopy. The green fluorescence of 1-3 is modulated by photoinduced electron transfer (PET) and internal charge transfer (ICT) mechanisms, and by solvent polarity. In 1 : 1 (v/v) methanol/water, logic gates 1 and 2 emit with Φf = 0.21 and 0.28, and bind with pβNa+ = 1.6 and pβK+ = 2.6, respectively, and pβH+ = 7.4 ± 0.1. In water, logic gates 1 and 2 emit with Φf = 0.14 and 0.26, and bind with pβNa+ = 0.86 and pβK+ = 1.6, respectively, and pβH+ = 8.1 ± 0.1. The measured pβNa+ are significantly lower than reported for analogous classic anthracene-based Na+, H+-driven AND logic gates indicating a stronger Na+ binding interaction, which is attributed to direct interaction with one carbonyl moiety within the aminonaphthalimide. Supporting evidence is provided by DFT calculations. Furthermore, we illustrate an example of logic function modulation by a change in solvent polarity. In 1 : 1 (v/v) methanol/water, molecules 1 and 2 function as Na+, H+ and K+, H+-driven AND logic gates. In water, the molecules function as single input H+-driven YES logic gates, while consideration as two-input devices, 1 and 2 function as AND-INH-OR logic arrays. |
| تواريخ الأحداث: |
Date Created: 20200403 Date Completed: 20210415 Latest Revision: 20210415 |
| رمز التحديث: |
20221213 |
| DOI: |
10.1039/d0ob00059k |
| PMID: |
32236273 |
| قاعدة البيانات: |
MEDLINE |
