Supporting Information
Supporting Information File 1: Experimental procedures, computational details and xyz coordinates, X-ray information including CCDC numbers and copies of 1H and 13C NMR spectra. | ||
Format: PDF | Size: 2.0 MB | Download |
Cite the Following Article
Scalable synthesis of 5,11-diethynylated indeno[1,2-b]fluorene-6,12-diones and exploration of their solid state packing
Bradley D. Rose, Peter J. Santa Maria, Aaron G. Fix, Chris L. Vonnegut, Lev N. Zakharov, Sean R. Parkin and Michael M. Haley
Beilstein J. Org. Chem. 2014, 10, 2122–2130.
https://doi.org/10.3762/bjoc.10.219
How to Cite
Rose, B. D.; Santa Maria, P. J.; Fix, A. G.; Vonnegut, C. L.; Zakharov, L. N.; Parkin, S. R.; Haley, M. M. Beilstein J. Org. Chem. 2014, 10, 2122–2130. doi:10.3762/bjoc.10.219
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Wang, J.; Wu, L.; Wang, Q. Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives. Chinese Journal of Organic Chemistry 2023, 43, 223. doi:10.6023/cjoc202206038
- Fregoso, G.; Rupasinghe, G. S.; Shahi, M.; Thorley, K.; Parkin, S.; Paterson, A. F.; Anthony, J. Functionalized anthrathienothiophenes: synthesis, properties, and integration into OFETs. Journal of Materials Chemistry C 2022, 10, 14439–14443. doi:10.1039/d2tc02977d
- Dibdalli, Y.; Gaete, J.; Valdebenito, C.; Arroyo, J. L.; Martínez, I.; Abarca, G.; Morales-Verdejo, C. Bimetallic ruthenium compound derived from 6,12-dihydroindeno[1,2-b]fluorene ligand as burning rate catalyst for solid rocket motor propellant. Journal of Organometallic Chemistry 2022, 973-974, 122408. doi:10.1016/j.jorganchem.2022.122408
- Can, A.; Facchetti, A.; Usta, H. Indenofluorenes for organic optoelectronics: the dance of fused five- and six-membered rings enabling structural versatility. Journal of Materials Chemistry C 2022, 10, 8496–8535. doi:10.1039/d2tc00684g
- Nishida, M.; Lee, D.; Shintani, R. Intermolecular Three-Component Synthesis of Fluorene Derivatives by a Rhodium-Catalyzed Stitching Reaction/Remote Nucleophilic Substitution Sequence. The Journal of organic chemistry 2020, 85, 8489–8500. doi:10.1021/acs.joc.0c00790
- Nishida, M.; Shintani, R. Convergent Synthesis of Fluorene Derivatives by a Rhodium‐Catalyzed Stitching Reaction/Alkene Isomerization Sequence. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 7475–7479. doi:10.1002/chem.201901519
- Mishra, S.; Lohr, T. G.; Pignedoli, C. A.; Liu, J.; Berger, R.; Urgel, J. I.; Müllen, K.; Feng, X.; Ruffieux, P.; Fasel, R. Tailoring Bond Topologies in Open-Shell Graphene Nanostructures. ACS nano 2018, 12, 11917–11927. doi:10.1021/acsnano.8b07225
- Tasior, M.; Hassanein, K.; Mazur, L. M.; Sakellari, I.; Gray, D.; Farsari, M.; Samoc, M.; Santoro, F.; Ventura, B.; Gryko, D. T. The role of intramolecular charge transfer and symmetry breaking in the photophysics of pyrrolo[3,2-b]pyrrole-dione. Physical chemistry chemical physics : PCCP 2018, 20, 22260–22271. doi:10.1039/c8cp03755h
- Hacker, A. S.; Pavano, M.; Wood, J. E.; Immoos, C. E.; Hashimoto, H.; Genis, S. P.; Frantz, D. K. Synthesis and Electronic Properties of Fluoreno[2,1-a]fluorenedione and Fluoreno[1,2-a]fluorenedione. The Journal of organic chemistry 2017, 83, 510–515. doi:10.1021/acs.joc.7b02699
- Petersen, J. F.; Frederickson, C. K.; Marshall, J. L.; Rudebusch, G. E.; Zakharov, L. N.; Hammerich, O.; Haley, M. M.; Nielsen, M. B. Expanded Indacene–Tetrathiafulvalene Scaffolds: Structural Implications for Redox Properties and Association Behavior. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 13120–13130. doi:10.1002/chem.201702347
- Hasegawa, M.; Endo, Y.; Honda, Y.; Mazaki, Y. π-Extended Tetrathiafulvalene Analogue with Dicyano Dihydro-s-indacene Core Leading to Facile Oxidation, Metallic Luster, and Solvatochromic Properties. Chemistry Letters 2017, 46, 964–967. doi:10.1246/cl.170257
- Marshall, J. L.; Uchida, K.; Frederickson, C. K.; Schütt, C.; Zeidell, A. M.; Goetz, K. P.; Finn, T. W.; Jarolimek, K.; Zakharov, L. N.; Risko, C.; Herges, R.; Jurchescu, O. D.; Haley, M. M. Indacenodibenzothiophenes: synthesis, optoelectronic properties and materials applications of molecules with strong antiaromatic character. Chemical science 2016, 7, 5547–5558. doi:10.1039/c6sc00950f
- Marshall, J. L.; O’Neal, N. J.; Zakharov, L. N.; Haley, M. M. Synthesis and Characterization of Two Unsymmetrical Indenofluorene Analogues: Benzo[5,6]-s-indaceno[1,2-b]thiophene and Benzo[5,6]-s-indaceno[2,1-b]thiophene. The Journal of organic chemistry 2016, 81, 3674–3680. doi:10.1021/acs.joc.6b00340
- Marshall, J. L.; Haley, M. M. Organic Redox Systems; Wiley, 2015; pp 311–358. doi:10.1002/9781118858981.ch10
- Haley, M. M. Origins of the Indenofluorene Project: Serendipity and Other Surprises. Chemical record (New York, N.Y.) 2015, 15, 1140–1143. doi:10.1002/tcr.201510004
- Frederickson, C. K.; Haley, M. M. Synthesis and Optoelectronic Properties of Indeno[1,2-b]fluorene-6,12-dione Donor–Acceptor–Donor Triads. The Journal of organic chemistry 2014, 79, 11241–11245. doi:10.1021/jo502009p
- Xiao, C.; Jiang, W.; Li, X.; Hao, L.; Liu, C.; Wang, Z. Laterally expanded rylene diimides with uniform branched side chains for solution-processed air stable n-channel thin film transistors. ACS applied materials & interfaces 2014, 6, 18098–18103. doi:10.1021/am504984z