Functionalization of Quinoxalines by Using TMP Bases: Preparation of Tetracyclic Heterocycles with High Photoluminescene Quantum Yields
Tetracyclic heterocycles that exhibit high photoluminescence quantum yields were synthesized by anellation reactions of mono‐, di‐, and trifunctionalized 2,3‐dichloroquinoxalines. Thus, treatment of 2,3‐dichloroquinoxaline with TMPLi (TMP=2,2,6,6‐tetramethylpiperidyl) allows a regioselective lithiation in position 5. Quenching with various electrophiles (iodine, (BrCl 2 C) 2 , allylic bromide, acid chloride, aryl iodide) leads to 5‐functionalized 2,3‐dichloroquinoxalines. Further functionalization in positions 6 and 8 can be achieved by using TMPLi or TMPMgCl ⋅ LiCl furnishing a range of new di‐ and tri‐functionalized 2,3‐dichloroquinoxalines. The chlorine atoms are readily substituted by anellation with 1,2‐diphenols or 1,2‐dithiophenols leading to a series of new tetracyclic compounds. These materials exhibit strong, tunable optical absorption and emission in the blue and green spectral region. The substituted O‐heterocyclic compounds exhibit particularly high photoluminescence quantum yields of up to 90 %, which renders them interesting candidates for fluorescence imaging applications. Light up : Treatment of 2,3‐dichloroquinoxaline with 2,2,6,6‐tetramethylpiperidyl (TMP)‐bases allows a regioselective functionalization of positions 5, 6 and 8. After these functionalizations, substitution of the chlorine atoms by various anellation reactions leads to a series of novel O‐ or S‐heterocyclic tetracycles that exhibit tunable optical properties with high molecular extinction coefficients and strong photoluminescence in the blue and green spectral regions..
| Medienart: |
Artikel |
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| Erscheinungsjahr: |
2015 |
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| Erschienen: |
2015 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:21 |
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| Enthalten in: |
Chemistry - a European journal - 21(2015), 3, Seite 1102-1107 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Nafe, Julia [VerfasserIn] |
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| Links: |
Volltext |
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| doi: |
10.1002/chem.201405240 |
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OLC1960624814 |
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| 245 | 1 | 0 | |a Functionalization of Quinoxalines by Using TMP Bases: Preparation of Tetracyclic Heterocycles with High Photoluminescene Quantum Yields |
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| 520 | |a Tetracyclic heterocycles that exhibit high photoluminescence quantum yields were synthesized by anellation reactions of mono‐, di‐, and trifunctionalized 2,3‐dichloroquinoxalines. Thus, treatment of 2,3‐dichloroquinoxaline with TMPLi (TMP=2,2,6,6‐tetramethylpiperidyl) allows a regioselective lithiation in position 5. Quenching with various electrophiles (iodine, (BrCl 2 C) 2 , allylic bromide, acid chloride, aryl iodide) leads to 5‐functionalized 2,3‐dichloroquinoxalines. Further functionalization in positions 6 and 8 can be achieved by using TMPLi or TMPMgCl ⋅ LiCl furnishing a range of new di‐ and tri‐functionalized 2,3‐dichloroquinoxalines. The chlorine atoms are readily substituted by anellation with 1,2‐diphenols or 1,2‐dithiophenols leading to a series of new tetracyclic compounds. These materials exhibit strong, tunable optical absorption and emission in the blue and green spectral region. The substituted O‐heterocyclic compounds exhibit particularly high photoluminescence quantum yields of up to 90 %, which renders them interesting candidates for fluorescence imaging applications. Light up : Treatment of 2,3‐dichloroquinoxaline with 2,2,6,6‐tetramethylpiperidyl (TMP)‐bases allows a regioselective functionalization of positions 5, 6 and 8. After these functionalizations, substitution of the chlorine atoms by various anellation reactions leads to a series of novel O‐ or S‐heterocyclic tetracycles that exhibit tunable optical properties with high molecular extinction coefficients and strong photoluminescence in the blue and green spectral regions. | ||
| 540 | |a Nutzungsrecht: © 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim | ||
| 540 | |a © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | ||
| 650 | 4 | |a metalation | |
| 650 | 4 | |a photoluminescence | |
| 650 | 4 | |a anellation | |
| 650 | 4 | |a functionalization | |
| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a quantum yield | |
| 650 | 4 | |a Heterocyclic Compounds - chemistry | |
| 650 | 4 | |a Organometallic Compounds - chemistry | |
| 650 | 4 | |a Piperidines - chemistry | |
| 650 | 4 | |a Quinoxalines - chemistry | |
| 650 | 4 | |a Heterocyclic Compounds - chemical synthesis | |
| 650 | 4 | |a Fluorescence | |
| 700 | 1 | |a Herbert, Simon |4 oth | |
| 700 | 1 | |a Auras, Florian |4 oth | |
| 700 | 1 | |a Karaghiosoff, Konstantin |4 oth | |
| 700 | 1 | |a Bein, Thomas |4 oth | |
| 700 | 1 | |a Knochel, Paul |4 oth | |
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| 856 | 4 | 1 | |u http://dx.doi.org/10.1002/chem.201405240 |3 Volltext |
| 856 | 4 | 2 | |u http://onlinelibrary.wiley.com/doi/10.1002/chem.201405240/abstract |
| 856 | 4 | 2 | |u http://www.ncbi.nlm.nih.gov/pubmed/25404387 |
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