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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

List of Table

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

List of Figure

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

List of Scheme

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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