1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Spectral Characterization
2.3. Molecular Structure
3. Experimental
3.1. General Information
3.2. Synthesis and Characterization
3.2.1. General Procedure for the Synthesis of 2-Benzoylhydrazinecarbothioamide Derivatives (2a–e)
3.2.2. General Procedure for the Synthesis of 2-Amino-1,3,4-thiadiazole Derivatives (3a–e)
3.2.3. General Procedure for the Synthesis of 2-(4-Aminophenylazo)-5-phenyl-1,3,4-thiadiazole Derivatives (4a–e)
3.2.4. General procedure for the synthesis of 2-[4-(N,N-dimethylamino)phenylazo]-5-phenyl-1,3,4-thiadiazole derivatives (5a–e)
3.2.5. General Procedure for the Synthesis of 2-(4-Hydroxyphenylazo)-5-phenyl-1,3,4-thiadiazole Derivatives (6a–e)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 4a–e, 5a–e, 6a–e are available from the authors. |
λmax (nm) | The Most Important Orbitals Involved in Electronic Transitions | Character of Transition | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Experimental | Calculated | ||||||||||
4 (G=NH2) | |||||||||||
a | b | c | d | e | a | b | c | d | e | ||
237 (3.95) | 256 (4.05) | 267 (4.07) | 249 (3.90) | 248 (4.02) | 261.44 (0.0909) | 276.70 (0.1045) | 237.50 (0.0536) | 256.39 (0.0432) | 270.17 (0.2800) | (a, e)H-2→L+1 (b)H→L+2 (c)H-2→L+2 (d)H-8→L | (a, e)n(NH2)/π→π* (b)n(NH2)/n(MeO)/π→π*(C6-rings) (c)n(NH2)/n(NO2)/π→π* (d)n(Br)/π(S-ring)→π* |
262.74 (0.0776) | 280.67 (0.2599) | 253.28 (0.0806) | 274.45 (0.3976) | 273.29 (0.1360) | (a)H-6→L (b)H-1→L+1 (c)H-6→L+1 (d)H-2→L+1 (e) H→L+2 | (a)n(NH2)/π→π* (b)n(NH2)/n(MeO)/π→π* (c)π→π* (d)n(Br)/n(NH2)/π→π* (e)n(NH2)/π→π*(C6-rings) | |||||
266.87 (0.1051) | 268.23 (0.0893) | (a)H→L+3 (c)H→L+4 | (a, c)n(NH2)/π→π*(C6-rings) | ||||||||
272.57 (0.1083) | (a)H→L+2 | (a)n(NH2)/π→π*(C6-rings) | |||||||||
285 (3.72) | 286 (3.88) | 286 (3.63) | 284 (3.79) | ||||||||
316 (3.56) | 319 (3.78) | 321 (4.03) | 318 (3.56) | 319 (3.68) | 325.66 (0.0203) | 322.13 (0.0500) | 312.40 (0.0522) | 333.77 (0.0204) | 324.73 (0.0294) | (a, b, d, e)H→L+1 (c)H-2→L+1 | (a, c, e)n(NH2)/π→π* (b)n(NH2)/n(MeO)/π→π* (d)n(Br)/n(NH2)/π→π* |
344.08 (0.1372) | (c)H-2→L | (c)n(NH2)/π→π* | |||||||||
491 (4.52) | 491 (4.46) | 507 (4.35) | 496 (4.41) | 492 (4.47) | 383.91 (0.1281) | 428.57 (0.7203) | (b)H-1→L (c)H→L+1 | (b)n(NH2)/n(MeO)/π→π* (c)n(NH2)/π→π* | |||
459.54 (1.4831) | 478.70 (1.3233) | 529.34 (0.8884) | 464.44 (1.4918) | 464.82 (1.4522) | H→L | (a, c, e)n(NH2)/π→π* (b) n(NH2)/n(MeO)/π→π* (d)n(Br)/n(NH2)/π→π* | |||||
5 (G=NMe2) | |||||||||||
a | b | c | d | e | a | b | c | d | e | ||
243 (3.96) | 256 (3.83) | 249 (3.73) | 251 (3.80) | 245 (4.06) | 264.95 (0.1359) | 278.83 (0.0592) | 241.40 (0.0442) | 256.30 (0.0430) | 270.21 (0.0655) | (a)H-2→L+1 (b, e) H-1→L+1 (c)H-2→L+2 (d)H-8→L | (a)π→π* (b) n(MeO)/n(NMe2)/π→π* (c)n(NO2)/π→π* (d)n(Br)/π→π* (e)σ(t-Bu)/n(Me2)/π→π* |
275.87 (0.1374) | 283.75 (0.1408) | 261.09 (0.0967) | 274.64 (0.1508) | 270.38 (0.0853) | (a)H-6→L (b)H→L+2 (c)H-6→L+1 (d)H-2→L+1 (e)H-1→L+1 | (a, c)π→π* (b)n(MeO)/n(NMe2)/π→π*(C6-ring near MeO) (d)n(Br)/n(NMe2)/π→π* (e)σ(t-Bu)/n(Me2)/π→π* | |||||
281.40 (0.0925) | 287.77 (0.2354) | 277.34 (0.1087) | 282.30 (0.2530) | 279.49 (0.2116) | (a)H→L+3 (b, d)H-5→L (c)H→L+4 (e)H-6→L | (a)n(NMe2)/π→π* (b)n(MeO)/π→π* (c)n(NMe2)/π→π*(C6-ring near NMe2) (d)n(Br)/π→π* (e)σ(t-Bu)/π→π* | |||||
281.87 (0.0869) | (e)H→L+2 | (e)n(NMe2)/π→π*(C6-rings) | |||||||||
293 (3.79) | 293 (3.73) | 299 (3.85) | 290 (3.61) | 295 (3.92) | |||||||
320 (3.68) | 334 (3.46) | 325 (3.49) | 323 (3.80) | 337.91 (0.0197) | 333.19 (0.0329) | 353.80 (0.1689) | 346.81 (0.0206) | 336.73 (0.0263) | (a, b, d, e)H→L+1 (c)H-2→L | (a, d, e)n(NMe2)/π→π* (b)n(MeO)/n(NMe2)/π→π* (c)n(NO2)/π→π* | |
515 (4.50) | 515 (4.25) | 530 (3.95) | 520 (4.30) | 515 (4.41) | 393.91 (0.0395) | 453.15 (0.8353) | (b)H-1→L (c)H→L+1 | (b)n(MeO)/n(NMe2)/π→π* (c)n(NMe2)/π→π* | |||
483.86 (1.4831) | 497.00 (1.1993) | 568.89 (0.8657) | 488.69 (1.5864) | 487.35 (1.5439) | H→L | (a, c, d, e)n(NMe2)/π→π* (b)n(MeO)/n(NMe2)/π→π* | |||||
6 (G=OH) | |||||||||||
a | b | c | d | e | a | b | c | d | e | ||
220.52 (0.0983) | (b)H-4→L+1 | (b)π(C6-ring near OH)→π* | |||||||||
236 (4.00) | 231 (3.68) | 234.73 (0.0439) | 232.01 (0.0382) | (a)H→L+3 (c)H-2→L+2 | (a)n(OH)/π→π*(C6-ring near S-ring) (c)n(NO2)/(OH)/π→π* | ||||||
256 (3.90) | 254 (4.04) | 260 (3.72) | 245 (4.04) | 243 (4.10) | 251.23 (0.0758) | 234.51 (0.0525) | 249.20 (0.0821) | 238.98 (0.0306) | 234.61 (0.0464) | (a, e)H→L+2 (b)H-3→L+1 (c)H-8→L (d)H-4→L+1 | (a)n(OH)/π→π*(C6-ring near OH) (b)π(C6-ring near MeO)→π* (c)n(NO2)/(OH)/π→π* (d)π(C6-rings)→π* (e)σ(t-Bu)/n(OH)/π→π*(C6-ring near t-Bu) |
254.98 (0.1078) | 271.99 (0.1002) | 264.75 (0.0369) | 251.23 (0.0556) | 265.07 (0.2413) | (a)H-2→L+1 (b, c, e)H-6→L (d)H→L+3 | (a, c)n(OH)/π→π* (b)n(MeO)/n(OH)/π→π* (d)n(Br)/n(OH)/π→π*(C6-ring near OH) (e)σ(t-Bu)/n(OH)/π→π* | |||||
262.06 (0.1766) | 266.81 (0.1192) | (a)H-6→L+1 (d)H-2→L+1 | (a)n(OH)/π→π* (d)n(Br)/n(OH)/π→π* | ||||||||
270.78 (0.1692) | (d)H-6→L | (d)n(Br)/n(OH)/π→π* | |||||||||
298 (3.54) | 291 (3.74) | 290 (3.76) | 290 (3.64) | 297.41 (0.0427) | 302.67 (0.1542) | 304.17 (0.0596) | 298.30 (0.0985) | (a, b, c, e)H→L+1 | (a)n(OH)/π→π* (b)n(MeO)/n(OH)/π→π* (d)n(Br)/n(OH)/π→π* (e)σ(t-Bu)/n(OH)/π→π* | ||
325.44 (0.0438) | (a)H-4→L | (a)π(C6-ring near OH)→π* | |||||||||
310 (3.74) | 305.19 (0.1361) | (c)H-2→L+1 | (c)n(NO2)/(OH)/π→π* | ||||||||
405 (4.46) | 415 (4.35) | 410 (4.13) | 409 (4.28) | 409 (3.96) | 341.08 (0.0630) | (c)H-3→L | (c)π(C6-ring near OH)→π* | ||||
345.44 (0.0461) | 370.43 (0.3618) | 385.35 (0.2630) | 355.56 (0.0770) | 355.42 (0.1288) | (a, d, e)H-2→L (b)H-1→L (c)H-1→L+1 | (a, c)n(OH)/π→π* (b)n(MeO)/n(OH)/π→π* (d)n(Br)/n(OH)/π→π* (e)σ(t-Bu)/n(OH)/π→π* | |||||
432.77 (1.1904) | 471.46 (0.9677) | 458.02 (1.1983) | 439.27 (1.2728) | 444.00 (1.1983) | H→L | (a, c)n(OH)/π→π* (b)n(MeO)/n(OH)/π→π* (d)n(Br)/n(OH)/π→π* (e)σ(t-Bu)/n(OH)/π→π* |
i—j | dij [Å] | i—j—k | αijk [°] | i—j—k | αijk [°] |
---|---|---|---|---|---|
S1—C1 | 1.7462(14) | C1—S1—C2 | 86.22(7) | C2—C11—C16 | 122.25(13) |
S1—C2 | 1.7366(14) | S1—C2—N2 | 114.29(11) | C5—C6—N5 | 121.16(12) |
C1—N1 | 1.3092(18) | C2—N2—N1 | 112.80(12) | C7—C6—N5 | 121.27(12) |
C2—N2 | 1.3124(18) | N2—N1—C1 | 112.25(12) | C6—N5—C9 | 120.76(12) |
N1—N2 | 1.3757(17) | N1—C1—S1 | 114.42(11) | C6—N5—C10 | 120.34(12) |
C1—N3 | 1.3821(18) | N1—C1—N3 | 120.62(13) | C9—N5—C10 | 118.16(12) |
N3—N4 | 1.2907(16) | S1—C1—N3 | 124.91(10) | C13—C14—O1 | 115.86(12) |
N4—C3 | 1.3851(18) | C1—N3—N4 | 111.67(11) | C15—C14—O1 | 124.38(13) |
C2—C11 | 1.4651(19) | N3—N4—C3 | 115.29(11) | C14—O1—C17 | 117.14(11) |
N5—C6 | 1.3520(18) | N4—C3—C4 | 125.47(12) | ||
N5—C9 | 1.4635(18) | N4—C3—C8 | 116.30(12) | ||
N5—C10 | 1.4606(18) | S1—C2—C11 | 122.98(10) | ||
O1—C14 | 1.3610(17) | N2—C2—C11 | 122.55(13) | ||
O1—C17 | 1.4346(17) | C2—C11—C12 | 118.81(13) |
D-H•••A | d(D-H) [Å] | d(H•••A) [Å] | d(D•••A) [Å] | <(DHA) [°] | Gda(n) |
---|---|---|---|---|---|
C9—H9A•••N1 i | 0.98 | 2.58 | 3.5351(1) | 165.4 | R22(22) |
C10—H10B•••O1 ii | 0.98 | 2.54 | 3.5031(1) | 166.3 | C(17) |
C16—H16•••S1 | 0.95 | 2.86 | 3.2088(1) | 102.7 | S(5) |
C7—H7•••Cg(C3) iii | 0.95 | 2.97 | 3.8190(1) | 148.8 | C(2) |
R(I)•••R(J) | d(Cg•••Cg) [Å] | α [°] | β [°] | dp [Å] |
---|---|---|---|---|
C3•••C3 iv | 3.6217(1) | 0 | 15.5 | 3.4908 |
C11•••C11 v | 3.5355(1) | 0 | 22.3 | 3.2703 |
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Kudelko, A.; Olesiejuk, M.; Luczynski, M.; Swiatkowski, M.; Sieranski, T.; Kruszynski, R. 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure. Molecules 2020, 25, 2822. https://doi.org/10.3390/molecules25122822
Kudelko A, Olesiejuk M, Luczynski M, Swiatkowski M, Sieranski T, Kruszynski R. 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure. Molecules. 2020; 25(12):2822. https://doi.org/10.3390/molecules25122822
Chicago/Turabian StyleKudelko, Agnieszka, Monika Olesiejuk, Marcin Luczynski, Marcin Swiatkowski, Tomasz Sieranski, and Rafal Kruszynski. 2020. "1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure" Molecules 25, no. 12: 2822. https://doi.org/10.3390/molecules25122822
APA StyleKudelko, A., Olesiejuk, M., Luczynski, M., Swiatkowski, M., Sieranski, T., & Kruszynski, R. (2020). 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure. Molecules, 25(12), 2822. https://doi.org/10.3390/molecules25122822