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(국문초록) 12
1. 서론 14
가. 연구배경 14
나. NH4+과 K+의 친화성 및 선택적 분자인식(이미지참조) 17
다. Isomeric Butylammonium Ions에 대한 분자인식 20
라. 연구 내용 및 방향 23
2. 실험 25
가. Materials and instruments 25
1) Materials 25
2) Instruments 26
나. Preparation of trinitrobenzenes 27
1) Preparation of 1, 3, 5-trimethyl-2, 4, 6-nitrobenzene (12a)²¹ 27
2) Preparation of 1, 3, 5-triethyl-2, 4, 6-nitrobenzene (12b)²¹ 27
다. Preparation of triaminobenzenes 28
1) Preparation of 1, 3, 5-triaminobenzene (13a)²² 28
2) Preparation of 1, 3, 5-triamino-2, 4, 6-trimethylbenzene (13b)²² 28
3) Preparation of 1, 3, 5-triamino-2, 4, 6-triethylbenzene (13c)²² 29
라. Preparation of triisothiocyanatobenzenes 29
1) Preparation of 1, 3, 5-triisothiocyanatobenzene (14a)²³ 29
2) Preparation of 1, 3, 5-triisothiocyanato-2, 4, 6-trimethylbenzene (14b) 30
3) Preparation of 1, 3, 5-triisothiocyanato-2, 4, 6-triethylbenzene (14c) 30
마. Preparation of Tri-N-(2-hydroxyethyl)-N'-phenyl thioureas 31
1) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-methylethyl)] ethyl-N'-phenylthiourea (15a) 31
2) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-phenyl)] ethyl-N'-phenylthiourea (15b) 31
3) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-methylethyl)] ethyl-N'-(2, 4, 6-trimethyl)phenylthiourea (15c) 32
4) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-phenyl)] ethyl-N'-(2, 4, 6-trimethyl)phenylthiourea (15d) 32
5) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-methylethyl)] ethyl-N'-(2, 4, 6-triethyl)phenylthiourea (15e) 33
6) Preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-phenyl)] ethyl-N'-(2, 4, 6-trimethyl)phenylthiourea (15f) 33
7) preparation of 1, 3, 5-tri-N-[(1S)-2-hydroxy-1-(1-methyl)] ethyl-N'-(2, 4, 6-trimethyl)phenylthiourea (15g) 34
바. Preparation of tripodal 2-aminooxazolines 35
1) Preparation of N, N', N"-Tris-(4-isopropyl-4, 5-dihydrooxazol-2-yl)-benzene-1, 3, 5-triamine (16a) 35
2) Preparation of N, N', N"-Tris-(4-phenyl-4, 5-dihydrooxazol-2-yl)-benzene-1, 3, 5-triamine (16b) 35
3) Preparation of N, N', N"-Tris-(4-isopropyl-4, 5-dihydrooxazol-2-yl)-2, 4, 6-trimethylbenzene-1, 3, 5-triamine (16c) 36
4) Preparation of N, N', N"-Tris-(4-phenyl-4, 5-dihydrooxazol-2-yl)-2, 4, 6-trimethylbenzene-1, 3, 5-triamine (16d) 37
5) Preparation of N, N', N"-Tris-(4-isopropyl-4, 5-dihydrooxazol-2-yl)-2, 4, 6-triethylbenzene-1, 3, 5-triamine (16e) 37
6) Preparation of N, N', N"-Tris-(4-phenyl-4, 5-dihydrooxazol-2-yl)-2, 4, 6-triethylbenzene-1, 3, 5-triamine (16f) 38
7) Preparation of N, N', N"-Tris-(4-methyl-4, 5-dihydrooxazol-2-yl)-2, 4, 6-triethylbenzene-1, 3, 5-triamine (16g) 39
사. Determination of association constants (Ka) by the ultraviolet method 40
아. ITC experiment 41
3. 결과 및 고찰 42
가. 새로운 Benzene-based tripodal 2-aminooxazolines 수용체의 합성 42
1) General procedure for the synthesis of the 1, 3, 5-trinitrobenzenes²¹ 42
2) General procedure for the synthesis of the 1, 3, 5-triaminobenzenes²² 44
3) Preparation of triisothiocyanatobenzenes²³ 45
4) Preparation of Tri-N-(2-hydroxyethyl)-N'-phenyl thioureas 46
5) Tripodal 2-aminooxazolines 수용체의 합성 48
나. NH4+과 K+의 친화성 및 선택적 분자인식(이미지참조) 50
1) Binding experiments 50
2) Picrate extraction method (Ka) 51
3) ITC experiment 54
가) Tripodal 2-aminooxazolines 수용체 (16)와 NH4+Pic(이미지참조) 55
나) Tripodal 2-aminooxazolines 수용체 (16)와 NH4+PF6(이미지참조) 58
다. Isomeric butylammonium ions에 대한 분자인식 61
1) Picrate Extraction method-Ka값 61
2) ITC experiment 64
4. 결론 67
5. 참고문헌 92
(Abstract) 95
Table 1. Preparation of trinitrobenzenes 43
Table 2. Preparation of triaminobenzenes 44
Table 3. Preparation of 1, 3, 5-triisothiocyanatocbenzenes 45
Table 4. Preparation of Tri-N-(2-hydroxyethyl)-N'-phenylthioureas 47
Table 5. Benzene-based tripodal 2-aminooxazolines 수용체 49
Table 6. Association constant (Ka×10³M1) of NH4+ and K+ ions (picrate salts) with receptors, obtained by UV spectroscopy (375 nm)a(이미지참조) 52
Table 7. Microcalorimeter로 측정한 수용체와 NH4+Pic 의 Association Constanta(이미지참조) 56
Table 8. Microcalorimeter로 측정한 수용체와 NH4+PF6의 Association Constanta(이미지참조) 59
Table 9. Association constant (Ka×10³M-¹) of isomeric BuNH4+ ions (picrate salts) with receptors, obtained by UV spectroscopy(375 nm)a(이미지참조) 62
Table 10. Microcalorimeter로 측정한 수용체와 Isomeric BuNH4+ ions의 Association Constanta(이미지참조) 65
Fig 1. Principle of biosensor 14
Fig 2. Principle of chemosensor 16
Fig 3. Crown ether receptors 18
Fig 4. Tripodal erceptors 19
Fig 5. Amine compounds 20
Fig 6. Adrenaline receptors 21
Fig 7. Benzene-based tripodal 2-aminooxazolines 52
Fig 8. TAO 수용체와 16g와 NH4+의 1TC 결과 54
Fig 9. Benzene-based tripodal 2-aminooxazolines 56
Fig 10. (a) TAO 수용체와 16e와 NH4+Pic 의 1TC 결과 (b) TAO 수용체와 16f와 NH4+Pic의 1TC 결과(이미지참조) 57
Fig 11. Benzene-based tripodal 2-aminooxazolines 59
Fig 12. (a) TAO 수용체 16e와 NH4+PF6의 1TC 결과 (b) TAO 수용체와 16f와 NH4+PF6의 1TC 결과 (c) TAO 수용체와 16g와 NH4+PF6의 1TC 결과(이미지참조) 60
Fig 13. Benzene-based tripodal 2-aminooxazolines 62
Fig 14. Benzene-based tripodal 2-aminooxazolines 65
Fig 15. (a) TAO 수용체와 16e와 n-BuNH3+ 의 1TC 결과 (b) TAO 수용체와 16f와 n-BuNH3+ 의 1TC 결과(이미지참조) 66
Fig 16. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-benzene-1,3,5-triamine (16a) 69
Fig 17. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-benzene-1,3,5-triamine (16a) 69
Fig 18. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-benzene-1,3,5-triamine (16b) 70
Fig 19. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-benzene-1,3,5-triamine (16b) 70
Fig 20. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16c) 71
Fig 21. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16c) 71
Fig 22. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16d) 72
Fig 23. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16d) 72
Fig 24. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16e) 73
Fig 25. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16e) 73
Fig 26. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1.3.5-triamine (16f) 74
Fig 27. ¹³C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16f) 74
Fig 28. ¹H NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16g) 75
Fig 29. 13C NMR spectrum of N,N',N''-Tris-(4-isopropyl-4,5-dihydrooxazol-2-yl)-2,4,6-trimwthylbenzene-1,3,5-triamine (16g) 75
Fig 30. TAO 수용체 16e와 NH4+Pic의(이미지참조) 1TC 결과 76
Fig 31. TAO 수용체 16f와 NH4+Pic의(이미지참조) 1TC 결과 77
Fig 32. TAO 수용체 16g와 NH4+Pic의(이미지참조) 1TC 결과 78
Fig 33. TAO 수용체 16c와 NH4+PF6의(이미지참조) 1TC 결과 79
Fig 34. TAO 수용체 16d와 NH4+PF6의(이미지참조) 1TC 결과 80
Fig 35. TAO 수용체 16e와 NH4+PF6의(이미지참조) 1TC 결과 81
Fig 36. TAO 수용체 16f와 NH4+PF6의(이미지참조) 1TC 결과 82
Fig 37. TAO 수용체 16g와 NH4+PF6의(이미지참조) 1TC 결과 83
Fig 38. TAO 수용체 16c와 n-BuNH3+의(이미지참조) 1TC 결과 84
Fig 39. TAO 수용체 16d와 n-BuNH3+의(이미지참조) 1TC 결과 85
Fig 40. TAO 수용체 16e와 n-BuNH3+의(이미지참조) 1TC 결과 86
Fig 41. TAO 수용체 16f와 n-BuNH3+의(이미지참조) 1TC 결과 87
Fig 42. TAO 수용체 16c와 t-BuNH3+의(이미지참조) 1TC 결과 88
Fig 43. TAO 수용체 16d와 t-BuNH3+의(이미지참조) 1TC 결과 89
Fig 44. TAO 수용체 16e와 t-BuNH3+의(이미지참조) 1TC 결과 90
Fig 45. TAO 수용체 16f와 t-BuNH3+의(이미지참조) 1TC 결과 91
Scheme 1. Receptors and n-BuNH3+(이미지참조) complex 21
Scheme 2. Receptors and arylalkylNH3+(이미지참조) complex 22
Scheme 3. Synthesis of tripodal 2-aminooxazolines 23
Scheme 4. Receptors and guest complex 24
Scheme 5. Preparation of trinitrobenzenes 43
Scheme 6. Preparation of triaminobenzenes 44
Scheme 7. Preparation of 1, 3, 5-triisothiocyanatobenzene 45
Scheme 8. Preparation of thioureas 46
Scheme 9. Preparation of Tri-N-(2-hydroxyethyl)-N'-phenylthioureas 47
Scheme 10. NaOH와 TsCl를 이용한 thioureas의 고리화 반응 48
Scheme 11. Benzene-based Tripodal 2-Aminooxazolines 수용체 49
Scheme 12. Receptor 16과 NH+(이미지참조)의 complex 53
Scheme 13. Receptor 16f와 n-BuNH3+(이미지참조)의 complex 63
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