A Review on the Synthesis of Fluorescent Five- and Six-Membered Ring Azaheterocycles
Abstract
:1. Introduction
2. Synthesis and Fluorescent Properties of Five- and Six-Membered Ring Azaheterocycles
2.1. Five Membered Ring Azaheterocycles
2.2. Six Membered Ring Azaheterocycles
2.3. Fused Azaheterocycles
2.4. Our Recent Contribution to the Field
3. Concluding Remarks
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | λabs (nm) | εmax (L·mol−1·cm−1) | λem (nm) | Φfl (%) | τ (ns) | kf (107·s−1) | Knr (107·s−1) |
---|---|---|---|---|---|---|---|
5aa | 338 | 20,700 ± 300 | 407 | 72 ± 4 | 7.4 ± 0.1 | 9.54 ± 0.10 | 3.89 ± 0.04 |
351 | 23,700 ± 300 | ||||||
377 | 6900 ± 200 | ||||||
397 | 8200 ± 200 | ||||||
5ba | 342 | 16,700 ± 200 | 424 | 69 ± 2 | 6.4 ± 0.1 | 10.77 ± 0.05 | 4.84 ± 0.02 |
354 | 20,000 ± 200 | ||||||
384 | 6500 ± 100 | ||||||
402 | 7500 ± 100 |
Compound | λabs (nm) a | λem (nm) b | Φfl (%) c | Compound | λabs (nm) a | λem (nm) b | Φfl (%) c |
---|---|---|---|---|---|---|---|
10a | 259 | 316 | <0.1 | 11a | 281 | 316 | <0.1 |
10b | 266 | 316 | <0.1 | 11b | 278 | 317 | <0.1 |
10c | 263 | 317 | <0.1 | 11c | 279 | 316 | <0.1 |
10d | 272 | 316 | <0.1 | 11d | 282 | 316 | <0.1 |
10e | 272 | 317 | <0.1 | 11e | 283 | 316 | <0.1 |
10f | 261, 302 | 333, 420 (br) | <0.1 | 11f | 297 | 322 | <0.1 |
10g | 304 | 333, 420 (br) | <0.1 | 11g | 297 | 321 | <0.1 |
10h | 272 | 316 | 0.6 | 11h | 272 | 317 | <0.1 |
10i | 305 | 331, 475 (br) | 0.1 | 11i | 298 | 320 | <0.1 |
10j | 305 | 335, 464 (br) | 0.2 | 11j | 297 | 325 | <0.1 |
10k | 277 | 317, 352 (br) | <0.1 | 11k | 288 | 317 | <0.1 |
10l | 256 | 316 | 1.9 | 11l | 277 | 317 | <0.1 |
Compound | Yield [%] | λabs [nm] | λex [nm] | λem [nm] | Φfl [%] |
---|---|---|---|---|---|
71 | 270 | 390 | 480 | 34 | |
18 | 24 | 270 | 390 | 480 | 31 |
19 | 65 | 270 | 390 | 480 | 44 |
20 | 52 | 270 | 390 | 485 | 31 |
21 | 60 | 270 | 390 | 485 | 27 |
22 | 52 | 270 | 390 | 485 | 32 |
23 | 53 | 270 | 390 | 485 | 22 |
24 | 17 | 258 | 345 | 455 | 2 |
25 | 67 | 270 | 390 | 480 | 35 |
26 | 57 | 270 | 390 | 480 | 30 |
Compound | Yield [%] | EtOH | MeOH-HEPES (80:20) | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
λabs [nm] | log ε | λem [nm] | Φfl [%] | Δλ [nm] | λabs [nm] | log ε | λem [nm] | Φfl [%] | Δλ [nm] | |||
36a | Boc-Gly-OAcm | 69 | 360 | 3.90 | 435 | 9 | 75 | 362 | 3.48 | 423 | 12 | 61 |
36b | Boc-Ala-OAcm | 93 | 361 | 3.93 | 411 | 11 | 50 | 360 | 3.69 | 412 | 15 | 52 |
36c | Boc-Glu-OAcm | 19 | 361 | 4.04 | 433 | 8 | 72 | 362 | 3.57 | 433 | 11 | 71 |
36d | Boc-β-Ala-OAcm | 72 | 361 | 3.91 | 412 | 11 | 51 | 361 | 3.79 | 417 | 14 | 56 |
36e | Boc-GABA-OAcm | 49 | 361 | 3.97 | 424 | 4 | 63 | 360 | 3.94 | 424 | 11 | 64 |
Compound | UV-Vis Absorption | Fluorescence | |||||
---|---|---|---|---|---|---|---|
λabs [nm] | log ε | λem [nm] | Φfl [%] | τ [ns] | kf 107 [s−1] | knf 107 [s−1] | |
39a BZ-TPE | 332 | 4.43 | 480 | 53.7 | 3.5 | 15.3 | 13.2 |
39b PY-TPE | 340 | 4.57 | 481 | 42.6 | 3.3 | 12.1 | 16.3 |
39c PYM-TPE | 346 | 4.42 | 482 | 31.2 | 3.0 | 10.4 | 22.9 |
39d PYA-TPE | 363 | 4.51 | 484 | 14.6 | 2.0 | 7.3 | 42.7 |
39e PYD-TPE | 343 | 4.24 | 450 | 0.6 | 1.3 | 0.46 | 76.2 |
39f PTZ-TPE | 323 | 4.45 | 480 | 1.6 | 1.7 | 0.94 | 57.8 |
Dye | λabs [nm] | log ε | λabs [nm] | log ε | λem [nm] | Φfl [%] | τ [ns] | |
---|---|---|---|---|---|---|---|---|
A1 | 301 | 4.33 | 405 | 4.44 | 547 | 47 | 3.83 | |
A2 | 299 | 4.35 | 417 | 4.43 | 605 | <1 | 0.26 | |
A3 | 307 | 4.43 | 433 | 4.36 | n.d. | n.d. | n.d. | |
B1 | 303 | 4.40 | 425 | 4.47 | 593 | 40 | 2.99 | |
B2 | 302 | 4.40 | 439 | 4.46 | 611 | <1 | 0.13 | |
C1 | 302 | 4.32 | 426 | 4.36 | 601 | 8 | 1.26 | |
C2 | 301 | 4.38 | 433 | 4.46 | 630 | <1 | <0.1 * | |
D1 | 292 | 4.11 | 380 | 4.24 | 478 | 90 | 3.12 | |
D2 | 257 | 4.72 | 377 | 4.42 ** | 484 sh, | 507 | 2 | 0.11 |
D3 | 240 | 4.77 | 373 | 4.40 | 455 sh, | 470 | <1 | 0.13 |
Solvent | A2 | D1 | ||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
λabs [nm] | log ε | λem [nm] | Φfl [%] | Stokes Shift [cm−1] | τ [ns] | λabs [nm] | log ε | λem [nm] | Φfl [%] | Stokes Shift [cm−1] | τ [ns] | |
Heptane | 427 | 4.585 | 483, 512 | 63 | 3900 | 2.6 | 387 | 4.466 | 456, 464 | 97 | 4300 | 2.4 |
Dioxane | 425 | 4.441 | 530 | 59 | 4700 | 3.8 | 385 | 4.399 | 472 | 100 | 4800 | 2.7 |
CHCl3 | 428 | 4.422 | 561 | 40 | 5500 | 4.0 | 387 | 4.235 | 475 | 95 | 4800 | 2.9 |
THF | 425 | 4.485 | 552 | 43 | 5400 | 3.8 | 384 | 4.474 | 473 | 100 | 4900 | 2.8 |
MeOH | 421 | 4.456 | 581 | <1 | 6500 | 0.1 | 382 | * | 489 | 81 | 5700 | 3.3 |
CH3CN | 417 | 4.434 | 603 | 1 | 7400 | 0.1 | 380 | 4.244 | 475 | 90 | 5300 | 3.1 |
Compound | Fluorescence Quantum Yield | |||
---|---|---|---|---|
Acetonitrile | Ethyl Acetate | |||
280 nm | 313 nm | 280 nm | 313 nm | |
47a | 3.7 | 3.5 | 3.9 | 3.7 |
47b | 3.6 | 3.7 | 4.3 | 3.5 |
47c | 3.9 | 3.6 | 3.7 | 3.4 |
Compound | Solvent | c [mol dm3] | λabs [nm] | ε(λabs) [M−1 cm−1] | λem [nm] | Φfl [%] |
---|---|---|---|---|---|---|
53e | MCHX | 2.94 × 10−5 | 396 | 5315 | 436 | 1.0 |
THF | 4.68 × 10−5 | 399 | 3816 | 459 | 1.5 | |
ACN | 4.89 × 10−5 | 398 | 3865 | 461 | 2.1 | |
53f | MCHX | 3.68 × 10−5 | 402 | 5324 | 442 | 0.7 |
THF | 3.83 × 10−5 | 404 | 5175 | 467 | 3.4 | |
ACN | 4.02 × 10−5 | 406 | 4852 | 479 | 67.2 | |
53g | MCHX | 3.17 × 10−5 | 399 | 4051 | 443 | 1.0 |
THF | 3.43 × 10−5 | 397 | 4055 | 480 | 6.8 | |
ACN | 3.44 × 10−5 | 397 | 4156 | 483 | 11.6 |
Compound | Host | λem [nm] | Φfl [%] | τPF [ns] | τDF [μs] | DF/PF | EA [eV] | S1 [eV] | T1 [eV] | ΔEST [eV] |
---|---|---|---|---|---|---|---|---|---|---|
56 | Zeonex® | 527 | 25 | 13.24 ± 1.18 | 9.45 ± 0.98 | 6.08 | 0.024 | 2.46 | 2.27 | 0.19 |
CBP | 555 | 34 | 25.28 ± 1.06 | 1.06 ± 0.11 | 1.57 | 0.031 | 2.24 | 2.12 | 0.12 | |
TCTA | 555 | 26 | 32.29 ± 0.57 | 2.10 ± 0.44 | 1.20 | 0.026 | 2.25 | 2.07 | 0.19 | |
57 | Zeonex® | 521 | 8 | 8.68 ± 0.09 | 0.7 ± 0.06 | 5.16 | 0.062 | 2.37 | 2.26 | 0.11 |
CPB | 553 | 29 | 17.67 ± 0.18 | 2.7 ± 0.24 | 1.99 | 0.033 | 2.28 | 2.05 | 0.22 | |
TCTA | 551 | 14 | 26.81 ± 0.83 | 3.92 ± 0.32 | 1.14 | 0.037 | 2.26 | 2.05 | 0.21 | |
58 | Zeonex® | 507 | 6 | 7.27 ± 0.32 | 9.90 ± 0.76 | 3.15 | 0.061 | 2.44 | 2.34 | 0.10 |
CPB | 535 | 20 | 11.84 ± 0.42 | 10.9 ± 0.66 | 0.78 | 0.036 | 2.33 | 2.07 | 0.27 | |
TCTA | 529 | 10 | 32.45 ± 1.23 | 5.26 ± 0.71 | 1.17 | 0.034 | 2.34 | 2.09 | 0.25 |
Compound | Absorption | Emission | Reference | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
λabs1 [nm] | ε1 [L/(mol cm)] | λabs2 [nm] | ε2 [L/(mol cm)] | λex1 [nm] | λem1 [nm] | λex2 [nm] | λem2 [nm] | Δν1 [cm−1] | Δν2 [cm−1] | Φfl [%] | ||
66a | 293 | 49,337 | 386 | 105,456 | 268 | 453 | 383 | 454 | 15,238 | 4083 | 4.64 | [50] |
66b | 263 | 25,640 | 389 | 34,200 | 262 | 459 | 354 | 466 | 16,381 | 6789 | 6.42 | [50] |
66c | 262 | 87,480 | 381 | 144,430 | 262 | 462 | 381 | 463 | 16,552 | 4648 | 19.02 | [50] |
66d | 266 | 43,920 | 384 | 68,180 | 2658 | 462 | 389 | 466 | 15,668 | 4536 | 6.35 | [50] |
66e | 270 | 18,880 | 399 | 20,706 | 270 | 457 | 400 | 462 | 15,155 | 3354 | 0.18 | [50] |
66f | 290 | 38,272 | 383 | 68,795 | 290 | 435 | 380 | 446 | 11,494 | 3894 | 55.27 | [50] |
66g | 268 | 34,200 | 398 | 44,780 | 262 | 451 | 360 | 463 | 15,994 | 6179 | 3.47 | [50] |
66h | 262 | 65,250 | 380 | 77,820 | 263 | 430 | 380 | 460 | 14,767 | 4576 | 8.91 | [50] |
66i | 292 | 39,784 | 380 | 34,836 | 264 | 455 | 380 | 464 | 15,900 | 4764 | 15.37 | [50] |
66j | 260 | 40,740 | 381 | 44,950 | 329 | 478 | 358 | 472 | 9860 | 6740 | 11.85 | [49] |
Compound | R4 | Absorption | Emission | |||||||
---|---|---|---|---|---|---|---|---|---|---|
λabs1 [nm] | ε1 [L/(mol cm)] | λabs2 [nm] | ε2 [L/(mol cm)] | λex [nm] | λem [nm] | Δν1 [cm−1] | Δν2 [cm−1] | Φfl [%] | ||
69a | H | 268 | 23,300 | 396 | 39,100 | 396 | 462 | 15,668 | 3608 | 51.77 |
69b | H | 265 | 25,200 | 400 | 36,800 | 400 | 462 | 16,091 | 3355 | 38.26 |
69c | H | 275 | 29,090 | 397 | 47,900 | 397 | 458 | 14,530 | 3355 | 61.35 |
69d | H | 258 | 42,300 | 405 | 53,800 | 405 | 437 | 15,876 | 1808 | 42.40 |
69e | CO2Me | 261 | 44,620 | 386 | 46,960 | 386 | 463 | 16,716 | 6786 | 11.04 |
69f | CO2Et | 252 | 39,520 | 390 | 50,630 | 390 | 539 | 21,130 | 7088 | 2.64 |
69g | CO2Me | 242 | 42,770 | 392 | 57,930 | 392 | 440 | 18,595 | 6957 | 6.63 |
69h | CO2Et | 250 | 61,060 | 395 | 65,910 | 395 | 456 | 18,070 | 3387 | 2.99 |
69i | CO2Me | 242 | 25,600 | 396 | 27,850 | 396 | 450 | 19,100 | 3030 | 27.46 |
69j | CO2Me | 268 | 56,200 | 388 | 47,200 | 388 | 535 | 18,622 | 7116 | 3.24 |
Compound | Solvent | Emission λmax nm | Excitation λmax nm | τ ns | Φfl % |
---|---|---|---|---|---|
76a | MePh | 602 | 337, 430, 516 | 4.6 ± 0.5 | 14 |
MeCN | 598 | 405, 494 | 3.9 ± 0.5 | 8 | |
DCM | 590 | 329, 413, 502 | 5.5 ± 0.5 | 18 | |
MeOH | 507 | 295, 428 | 9.0 ± 0.5 | 76 | |
76b | MePh | 640 | 427, 528 | 1.0 ± 0.2 | 7 |
MeCN | 630 | 401, 498 | 1.0 ± 0.2 | 0.7 | |
DCM | 628 | 438, 500 | 1.0 ± 0.2 | 3 | |
MeOH | 530 | 292, 426 | 10.3 ± 0.5 | 47 | |
76c | MePh | 645 | 440, 539 | 1.4 ± 0.2 | 7.5 |
MeCN | 642 | 417, 513 | 1.5 ± 0.2 | 2.5 | |
DCM | 626 | 330, 420, 522 | 1.7 ± 0.2 | 9 | |
MeOH | 537 | 443 | 7.5 ± 0.5 | 81 |
Compound | Fluorescence (λmax, nm) (Quantum Yields (%)) | Absorption (λmax, nm) | ||||
---|---|---|---|---|---|---|
EtOH | CHCl3 | Cyclohexane | EtOH | CHCl3 | Cyclohexane | |
79a | 431 (70) | 430 (90) | 430 (83) | 343 | 351 | 355 |
79b | 431 (70) | 429 (90) | 430 (83) | 343 | 352 | 355 |
79c | 429 (63) | 431 (82) | 434 (76) | 356 | 362 | 366 |
79d | 446 (1) | 436 (8) | 433 (11) | 334 | 335 | 329 |
79e | 448 (2) | 439 (3) | 434 (-) | 334 | 334 | 329 |
79f | 451 (1) | 438 (7) | 436 (10) | 332 | 333 | 327 |
79g | 487 (1) | 471 (1) | insoluble | 374 | 375 | insoluble |
79h | 448 (4) | 431 (5) | 434 (8) | 314 | 319 | 322 |
80a | 430 (66) | 423 (91) | 416 (85) | 349 | 357 | 361 |
80b | 429 (66) | 422 (91) | 416 (85) | 349 | 358 | 361 |
80c | 436 (89) | 437 (76) | insoluble | 365 | 370 | insoluble |
80d | 442 (1) | 436 (5) | insoluble | 333 | 335 | insoluble |
80e | 430 (2) | 436 (7) | insoluble | 330 | 332 | insoluble |
80f | 433 (1) | 437 (4) | 432 (8) | 333 | 334 | 329 |
80g | 446 (4) | 430 (5) | 432 (9) | 315 | 319 | 322 |
80h | 446 (4) | 430 (4) | 432 (8) | 316 | 320 | 322 |
80i | 448 (3) | 432 (2) | insoluble | 319 | 322 | insoluble |
81b | 442 (2) | 439 (2) | insoluble | 326 | 321 | insoluble |
81c | 427 (1) | 439 (5) | insoluble | 316 | 304 | insoluble |
82a | 430 (9) | 427 (18) | 415 (40) | 470 | 479 | 496 |
82b | 430 (9) | 427 (18) | 415 (40) | 470 | 479 | 496 |
82c | 432 (3) | 424 (4) | 420 (4) | 485 | 488 | 508 |
82d | 433 (4) | 424 (4) | 419 (4) | 484 | 488 | 508 |
Compound | λmax (nm) [ε (L mol−1 cm−1) × 103] | Fluorescence Intensity | ||||
---|---|---|---|---|---|---|
Number of Absorption Maxima | ||||||
I | II | III | IV | V | ||
86a | 356.00 [2.65] | 347.00 [2.33] | 277.00 [30.33] | 264.00 [25.02] | 225.00 [11.30] | 6276.11 |
86b | 357.00 [2.93] | 337.00 [2.58] | 280.00 [32.95] | 263.00 [26.00] | 226.00 [11.90] | 6554.21 |
86c | 355.00 [2.93] | 341.00 [2.80] | 284.00 [30.23] | 265.00 [24.15] | 228.00 [11.91] | 7510.05 |
86d | 356.00 [3.00] | 340.00 [2.73] | 284.00 [31.68] | 264.00 [24.73] | 227.00 [11.75] | 8264.76 |
87a | 344.00 [3.50] | 340.00 [3.46] | 276.00 [31.15] | 264.00 [26.75] | 226.00 [7.45] | 5016.82 |
87b | 350.00 [3.18] | 335.00 [2.95] | 276.00 [32.38] | 264.00 [26.75] | 226.00 [11.51] | 5269.64 |
87c | 350.00 [3.18] | 335.00 [3.01] | 282.00 [30.21] | 265.00 [25.68] | 227.00 [6.00] | 6018.34 |
87d | 350.00 [3.31] | 334.00 [3.06] | 276.00 [34.46] | 264.00 [29.01] | 228.00 [12.33] | 6304.55 |
Compound | Fluorescence (λmax, nm) (Quantum Yields (%)) | Absorption (λmax, nm) | ||
---|---|---|---|---|
Cyclohexane | Dichloromethane | Cyclohexane | Dichloromethane | |
91 | 426 (24) | 432 (21) | 360 | 358 |
92 | 422 (25) | 426 (26) | 356 | 354 |
93 | 428 (7) | 441 (5) | 327 | 325 |
94 | 439 (6) | 446 (4) | 324 | 322 |
95 | 491 | - | 374 | 372 |
Compound | Fluorescence (λmax, nm) | Absorption (λmax, nm) | ||
---|---|---|---|---|
Cyclohexane | Trichloromethane | Cyclohexane | Trichloromethane | |
102a | 434 | 439 | 399 | 403 |
102b | 434 | 440 | 399 | 402 |
102c | 440 | 445 | 384 | 386 |
103a | 432 | 432 | 378 | 381 |
103b | 432 | 433 | 376 | 375 |
103c | 451 | 430 | 373 | 370 |
104c | 450 | 449 | 374 | 369 |
Compound | Fluorescence (λmax, nm) | Absorption (λmax, nm) | Quantum Yields (%) |
---|---|---|---|
105a | 443 | 394 | 22.11 |
105b | 431 | 391 | 18.64 |
105c | 444 | 412 | 15.92 |
105d | 433 | 393 | 17.09 |
107a | 430 | 406 | 9.34 |
107b | 435 | 387 | 7.17 |
107c | 430 | 409 | 8.99 |
107d | 445 | 393 | 5.30 |
Compound | Solvent | λabs [nm] | λem [nm] | Φfl [%] | τ1 [ns] | τ2 [ns] |
---|---|---|---|---|---|---|
112a | DCM | 352, 335, 320, 275, 244 | 356, 374, 392, 415sh | 28.37 | ||
DMSO | 353, 336, 321, 276 | 359, 376, 395, 415sh | 63.47 | 0.069 | 3.115 | |
112b | DCM | 358, 341, 325, 274, 246 | 363, 381, 401, 425sh | 20.10 | ||
DMSO | 358, 341, 325, 275 | 361, 382, 401, 425sh | 53.95 | 0.866 | 3.095 | |
112c | DCM | 358, 341, 324, 274, 247 | 363, 381, 401, 425sh | 31.28 | ||
DMSO | 358, 341, 325sh, 275 | 364, 382, 400, 425sh | 55.76 | 0.112 | 3.219 | |
113a | DCM | 338, 323, 309, 252 | 340, 356, 375, 395sh | 41.04 | ||
DMSO | 339, 324, 309 | 345, 361, 378 | 3.36 | 0.031 | 2.785 | |
113b | DCM | 338, 323, 309, 251 | 344, 360, 374, 400sh | 18.37 | ||
DMSO | 338, 324, 309 | 346, 360, 374 | 7.96 | 0.060 | 2.700 | |
113c | DCM | 338, 323, 309, 252 | 345, 359, 375, 400sh | 29.41 | ||
DMSO | 339, 323, 309 | 346, 359, 372 | 15.95 | 0.036 | 5.400 |
Compound | Φfl [%] | τ1 [ns] | τ2 [ns] | τ3 [ns] | f1 | f2 | f3 |
---|---|---|---|---|---|---|---|
114a | 38.71 | 4.41 | |||||
114b | 17.87 | 3.39 | |||||
114c | 16.89 | 0.48 | 9.35 | 0.23 | 0.77 | ||
114e | 75.42 | 4.00 | |||||
114f | 6.65 | 0.41 | 2.51 | 8.12 | 0.37 | 0.25 | 0.38 |
114g | 6.09 | 0.60 | 8.06 | 0.57 | 0.43 | ||
115a | 33.10 | 3.12 | |||||
115b | 6.16 | 0.76 | 4.45 | 0.94 | 0.06 | ||
115e | 4.43 | 3.73 |
Compound | pH | λex [nm] | λem [nm] | Stokes Shift [cm−1] |
---|---|---|---|---|
121 | 2.0 | 395 | 521 | 6123 |
5.0 | 539 | 6764 | ||
5.5 | 539 | 6764 | ||
6.0 | 539 | 6764 | ||
6.5 | 539 | 6764 | ||
7.0 | 539 | 6764 | ||
7.5 | 539 | 6764 | ||
8.0 | 539 | 6764 | ||
12.0 | 491, 526 | 4950, 6305 | ||
124 | 2.0 | 395 | 560 | 7459 |
5.0 | 486, 525 | 4740, 6269 | ||
5.5 | 480, 513 | 4483, 5823 | ||
6.0 | 480, 514 | 4483, 5861 | ||
6.5 | 480 | 4483 | ||
7.0 | 480 | 4483 | ||
7.5 | 481 | 4526 | ||
8.0 | 482 | 4570 | ||
12.0 | 482 | 4570 |
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Zbancioc, G.; Mangalagiu, I.I.; Moldoveanu, C. A Review on the Synthesis of Fluorescent Five- and Six-Membered Ring Azaheterocycles. Molecules 2022, 27, 6321. https://doi.org/10.3390/molecules27196321
Zbancioc G, Mangalagiu II, Moldoveanu C. A Review on the Synthesis of Fluorescent Five- and Six-Membered Ring Azaheterocycles. Molecules. 2022; 27(19):6321. https://doi.org/10.3390/molecules27196321
Chicago/Turabian StyleZbancioc, Gheorghita, Ionel I. Mangalagiu, and Costel Moldoveanu. 2022. "A Review on the Synthesis of Fluorescent Five- and Six-Membered Ring Azaheterocycles" Molecules 27, no. 19: 6321. https://doi.org/10.3390/molecules27196321