Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
-
Dörthe Jakobi
,
André Schumann
Abstract
In this study, we report on the syntheses of novel angular fused azaacenes. For this purpose, the synthesis of the bis-diamine 2 (TABEF) could be shortened and optimized. The condensation reaction of 2 with different types of 1,2-diketones yielded new azaacene derivatives of types 10, 11 and 12. Analogously, 2 was cyclized with thionyl chloride to give the piazthiol derivative 13. The optical and electrochemical properties of all new compounds were investigated by UV/Vis absorption, fluorescence emission spectroscopy and cyclovoltammetric measurements.
References
[1] E. J. Anthony, Angew. Chem. Int. Ed. 2008, 47, 452.10.1002/anie.200604045Suche in Google Scholar PubMed
[2] M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891.10.1021/cr030666mSuche in Google Scholar PubMed
[3] U. H. F. Bunz, Chem. Eur. J.2009, 15, 6780.10.1002/chem.200900990Suche in Google Scholar PubMed
[4] U. H. F. Bunz, Pure Appl. Chem. 2010, 82, 953.10.1351/PAC-CON-09-09-17Suche in Google Scholar
[5] G. J. Richards, J. P. Hill, T. Mori, K. Ariga, Org. Biomol. Chem.2011, 9, 5005.10.1039/c1ob05454fSuche in Google Scholar PubMed
[6] J. Li, Q. Zhang, ACS Appl. Mater. Interfaces2015, 7, 28049.10.1021/acsami.5b00113Suche in Google Scholar PubMed
[7] K. R. J. Thomas, A. Baheti, Mater. Technol.2013, 28, 71.10.1179/1753555712Y.0000000036Suche in Google Scholar
[8] T.-C. Lin, B.-K. Tsai, Y.-Y. Liu, M.-Y. Tsai, Eur. J. Org. Chem.2014, 28, 6163.10.1002/ejoc.201402622Suche in Google Scholar
[9] K. Zhang, Y. Dai. X. Zhang, Y. Xiao, Dyes Pigm.2014, 102, 1.10.1016/j.dyepig.2013.10.030Suche in Google Scholar
[10] E. Bindewald, R. Lorenz, O. Hübner, D. Brox, D.-P. Herten, E. Kaifer, H.-J. Himmel, Dalton Trans. 2015, 44, 3467.10.1039/C4DT03572KSuche in Google Scholar
[11] X. Li, Y. Xiao, X. Qian, Org. Lett.2008, 10, 2885.10.1021/ol801081wSuche in Google Scholar PubMed
[12] S. Rau, B. Schäfer, D. Gleich, E. Anders, M. Rudolph, M. Friedrich, H. Görls, W. Henry, J. G. Vos, Angew. Chem. Int. Ed.2006, 45, 6215.10.1002/anie.200600543Suche in Google Scholar PubMed
[13] B. A. D. Neto, A. A. M. Lapis, E. N. da Silva Jr, J. Dupont, Eur. J. Org. Chem.2013, 2013, 228.10.1002/ejoc.201201161Suche in Google Scholar
[14] K. M. Omer, S. Y. Ku, J. Z. Cheng, S. H. Chou, K. T. Wong, A. J. Bard, J. Am. Chem. Soc. 2011, 133, 5492.10.1021/ja2000825Suche in Google Scholar PubMed
[15] T. Miyazaki, M. Shibahara, J. Fujishige, M. Watanabe, K. Goto, T. Shinmyozu, J. Org. Chem.2014, 79, 11440.10.1021/jo5020273Suche in Google Scholar PubMed
[16] D. Jiang, S. Chen, Z. Xue, Y. Li, H. Liu, W. Yang, Y. Li, Dyes Pigm. 2016, 125, 100.10.1016/j.dyepig.2015.10.014Suche in Google Scholar
[17] D. M. Gampe, F. Nöller, V. G. Hänsch, S. Schramm, A. Darsen, S. H. Habenicht, S. Ehrhardt, D. Weiß, H. Görls, R. Beckert, Tetrahedron2016, 72, 3232.10.1016/j.tet.2016.04.046Suche in Google Scholar
[18] Y. Sun, C. Qu, H. Chen, M. He, C. Tang, K. Shou, S. Hong, M. Yang, Y. Jiang, B. Ding, Y. Xiao, L. Xing, X. Hong, Z. Cheng, Chem. Sci. 2016, 7, 6203.10.1039/C6SC01561ASuche in Google Scholar PubMed PubMed Central
[19] M. Bendikov, F. Wudl, Chem. Rev.2004, 104, 4891.10.1021/cr030666mSuche in Google Scholar PubMed
[20] A. M. Brouwer, Pure Appl. Chem. 2011, 83, 2213.10.1351/PAC-REP-10-09-31Suche in Google Scholar
[21] C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J.-L. Bredas, P. C. Ewbank, K. R. Mann, Chem. Mater. 2004, 16, 4436.10.1021/cm049391xSuche in Google Scholar
[22] C. M. Cardona, W. Li, A. E. Kaifer, D. Stockdale, G. C. Bazan, Adv. Mater.2011, 23, 2367.10.1002/adma.201004554Suche in Google Scholar PubMed
[23] D. M. Gampe, S. Schramm, M. Kaufmann, H. Görls, R. Beckert, New J. Chem.2016, 40, 10100.10.1039/C6NJ02544GSuche in Google Scholar
[24] M. Schaffroth, B. D. Lindner, V. Vasilenko, F. Rominger, U. H. F. Bunz, J. Org. Chem. 2013, 78, 3142.10.1021/jo400092rSuche in Google Scholar PubMed
©2018 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
Artikel in diesem Heft
- Frontmatter
- In this Issue
- Preface
- The role of iminium salts, imines and related compounds in chemistry
- Original Articles
- A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines
- Orthoamide und Iminiumsalze, XCII. Synthese und Reaktionen von Orthoamiden aus ethinylierten Terpenderivatena
- Orthoamide und Iminiumsalze, XCIII. Darstellung und Umsetzungen eines vinylogen Orthoamid-Derivats der Kohlensäure mit CH2-aciden Verbindungena
- Synthesis of functionalized pyrazole derivatives by regioselective [3+2] cycloadditions of N-Boc-α-amino acid-derived ynones
- Chemistry and spectroscopy of cross-conjugated and pseudo-cross-conjugated quinolinium-ethynyl-benzoate mesomeric betaines
- Integrating the fluorene substructure into azaacenes: syntheses of novel fluorophores
- Thermal metal-free [2+2] cycloaddition of acetylenedicarboxylates to polysubstituted butadienes
- Protic ionic liquids as catalysts for a three-component coupling/hydroarylation/dehydrogenation tandem reaction
- Review
- Iminiumsalz-Strukturen bei der durch Pyridoxalphosphat (Vitamin B6) katalysierten Bildung von Aromastoffen und Fehlaromen im Wein
