Optical Investigation of 2-amino-7-isocyanofluorene, a Novel Blue-Emitting Solvatochromic Dye
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Synthesis of 2-amino-7-isocyanofluorene (2,7-ICAF)
2.3. Characterization Methods
2.4. Density Functional Theory (DFT) Calculations
3. Results and Discussions
3.1. Synthesis of 2-amino-7-isocyanofluorene (2,7-ICAF)
3.2. Optical Characterization of 2,7-diaminofluorene (2,7-DAF) and 2-amino-7-isocyanofluorene (2,7-ICAF)
3.3. Investigation of the Solvatochromic Behavior of 2,7-DAF and 2,7-ICAF
3.4. Theoretical Results
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Solvent (εr) | 2,7-DAF | 2,7-ICAF | 4,4′-ICAB | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
λAbs (nm) | ε × 10−3 (M−1cm−1) | λEm (nm) | Φf (%) | λAbs (nm) | ε × 10−3 (M−1cm−1) | λEm (nm) | Φf (%) | λAbs (nm) | ε × 10−3 (M−1cm−1) | λEm (nm) | Φf (%) | |
Toluene (2.38) | 341 | 6.0 | 382 | 23 | 330 | 15.9 | 367 | 95 | 310 | 5.4 | 371 | 7 |
EtOAc (6.02) | 343 | 6.2 | 387 | 20 | 332 | 16.3 | 387 | 80 | 315 | 6.2 | 397 | 6 |
THF (7.58) | 345 | 5.8 | 392 | 18 | 338 | 16.9 | 390 | 82 | 319 | 5.1 | 396 | 7 |
DCM (8.93) | 340 | 7.0 | 381 | 1 | 328 | 16.5 | 384 | 70 | 307 | 6.1 | 390 | 7 |
Acetone (20.7) | 344 | 6.1 | 391 | 0.3 | 336 | 16.5 | 401 | 87 | 329 | 5.5 | 407 | 5 |
Methanol (32.7) | 334 | 5.8 | 395 | 21 | 326 | 17.1 | 411 | 5 | 308 | 4.7 | 419 | 1 |
Acetonitrile (37.5) | 343 | 6.3 | 390 | 21 | 330 | 18.4 | 405 | 82 | 310 | 5.9 | 410 | 6 |
DMSO (46.7) | 353 | 5.5 | 404 | 43 | 344 | 18.0 | 418 | 94 | 318 | 5.3 | 436 | 7 |
Water (80.1) | 327 | 7.2 | 397 | 2 | 322 | 14.9 | - | - | 298 | 5.1 | 458 | 0.1 |
y0 (cm−1) | aSA | bSB | cSP | dSdP | R2 | n | ||
---|---|---|---|---|---|---|---|---|
2,7-DAF | νem,max | 29,332 | −1080 | −2340 | −3516 | 51 | 0.88 | 8 |
Δνss | 2840 | 2116 | 551 | 308 | 55 | 0.99 | 9 | |
2,7-ICAF | νem,max | 32,902 | −2184 | −2516 | −6264 | −2155 | 0.90 | 8 |
Δνss | 1388 | 3401 | 9.95 | 3140 | 836 | 0.85 | 8 |
1,5-ICAN | 2,7-DAF | 2,7-ICAF | ||||
S0 | S1 | S0 | S1 | S0 | S1 | |
Bond length (Angstrom) | ||||||
-NH2 | 1.391 | 1.340 | 1.401 | 1.363 | 1.392 | 1.353 |
d(C-N)≡C | 1.389 | 1.358 | - | - | 1.389 | 1.357 |
d(N≡C) | 1.167 | 1.181 | - | - | 1.167 | 1.184 |
µ (Debye) | 7.35 | 8.61 | 1.39 | 1.74 | 8.84 | 10.9 |
abs (nm) | 380 (347) * | 481 (497) * | 339 (353) | 392 (404) | 343 (347) | 406 (417) |
NH2 angle | 342 | 360 | 340 | 356 | 343 | 360 |
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Kontra, B.; Mucsi, Z.; Vanyorek, L.; Nagy, M. Optical Investigation of 2-amino-7-isocyanofluorene, a Novel Blue-Emitting Solvatochromic Dye. Colorants 2024, 3, 86-98. https://doi.org/10.3390/colorants3020006
Kontra B, Mucsi Z, Vanyorek L, Nagy M. Optical Investigation of 2-amino-7-isocyanofluorene, a Novel Blue-Emitting Solvatochromic Dye. Colorants. 2024; 3(2):86-98. https://doi.org/10.3390/colorants3020006
Chicago/Turabian StyleKontra, Bence, Zoltán Mucsi, László Vanyorek, and Miklós Nagy. 2024. "Optical Investigation of 2-amino-7-isocyanofluorene, a Novel Blue-Emitting Solvatochromic Dye" Colorants 3, no. 2: 86-98. https://doi.org/10.3390/colorants3020006