none 10.1039/C6RA28567H Royal Society of Chemistry (RSC) The Royal Society of Chemistry 292 87697513 138446 20171121170855 10.1039 2024-04-17T22:46:10Z 2017-01-30T08:23:36Z 3 RSC Advances RSC Adv. 2046-2069 RSCACL 2017 7 14 New quinacridone derivatives with π-extended conjugation in central core Piotr Kurzep Faculty of Chemistry Warsaw University of Technology 00-664 Warsaw Poland Łukasz Skórka Faculty of Chemistry Warsaw University of Technology 00-664 Warsaw Poland Malgorzata Zagorska Faculty of Chemistry Warsaw University of Technology 00-664 Warsaw Poland Piotr A. Guńka Faculty of Chemistry Warsaw University of Technology 00-664 Warsaw Poland http://orcid.org/0000-0002-0977-5246 Marzena Banasiewicz Institute of Physics Polish Academy of Science 02-668 Warsaw Poland Bolesław Kozankiewicz Institute of Physics Polish Academy of Science 02-668 Warsaw Poland http://orcid.org/0000-0002-2507-2356 Irena Kulszewicz-Bajer Faculty of Chemistry Warsaw University of Technology 00-664 Warsaw Poland http://orcid.org/0000-0002-7936-5138

A novel synthetic strategy for the preparation of quinacridone derivatives with extended conjugation in central aromatic core is proposed allowing for fine tuning of their electronic properties.

A novel synthetic strategy for the preparation of quinacridone derivatives with extended conjugation in central aromatic core is proposed allowing for fine tuning of their electronic properties. Two new quinacridone derivatives with carbazole ( 1 ) and naphthalene ( 2 ) core are described, which are excellent candidates for optoelectronic applications as evidenced by their electrochemically determined redox properties combined with strong photoluminescence (the fluorescence quantum yield of 0.83 and the radiative rate constant of 90.2 × 10 7 s −1 in the case of 2 ).

2017 8627 8632 1 10.1039/rsc_crossmark_policy rsc.org true This document is Similarity Check deposited Supplementary Information Crystal Structure Data Piotr A. Guńka (ORCID) Piotr A. Guńka (ResearcherID) Bolesław Kozankiewicz (ORCID) Irena Kulszewicz-Bajer (ORCID) The Royal Society of Chemistry has an exclusive publication licence for this journal This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) Single-blind Received 22 December 2016; Accepted 23 January 2017; Version of Record published 30 January 2017 10.1039/C6RA28567H 20171121170855 https://xlink.rsc.org/?DOI=C6RA28567H http://pubs.rsc.org/en/content/articlepdf/2017/RA/C6RA28567H J. Phys. Chem. B Ye 109 8008 2005 10.1021/jp0444767 Org. Electron. Bi 11 1180 2010 10.1016/j.orgel.2010.04.015 J. Phys. Chem. C Wang 116 17796 2012 10.1021/jp305187m J. Mater. Chem. C Wang 1 5548 2013 10.1039/c3tc30803k Chem. Commun. Wang 51 11972 2015 10.1039/C5CC04469C RSC Adv. Wang 6 19308 2016 10.1039/C6RA01094F Appl. Phys. Lett. Głowacki 101 023305 2012 10.1063/1.4736579 Chem. Mater. Osaka 24 1235 2012 10.1021/cm300514z J. Mater. Chem. C Li 1 2021 2013 10.1039/c3tc00550j Org. Lett. Chen 17 6146 2015 10.1021/acs.orglett.5b03155 Polym. Chem. Li 6 3283 2015 10.1039/C5PY00103J Org. Electron. Chen 12 1126 2011 10.1016/j.orgel.2011.03.039 New J. Chem. Wang 36 1788 2012 10.1039/c2nj40306d Eur. J. Org. Chem. Mattiello 5723 2015 10.1002/ejoc.201500554 Chem. Commun. Pho 46 8210 2010 10.1039/c0cc01596b Macromolecules Liu 41 1162 2008 10.1021/ma071235z J. Phys. Chem. C Wang 111 9177 2007 10.1021/jp072488x Chem. Commun. Ortiz 444 2005 10.1039/b413684e J. Org. Chem. Takeda 79 9669 2014 10.1021/jo501800g J. Mater. Chem. A Chen 4 2169 2016 10.1039/C5TA09701K Org. Lett. Zou 17 3146 2015 10.1021/acs.orglett.5b01465 Adv. Mater. Keller 8 490 1996 10.1002/adma.19960080607 J. Org. Chem. Baudoin 62 5458 1997 10.1021/jo970496b Tetrahedron Lett. Jacquelin 46 2589 2005 10.1016/j.tetlet.2005.02.079 Synlett Lartia 4 610 2006 J. Solid State Electrochem. Karon 19 2601 2015 10.1007/s10008-015-2973-x J. Electroanal. Chem. Sioda 612 147 2008 10.1016/j.jelechem.2007.07.016 J. Am. Chem. Soc. Parker 98 98 1978 10.1021/ja00417a017 Pure Appl. Chem. Trasatti 58 955 1986 10.1351/pac198658070955 Adv. Mater. van der Poll 24 3646 2012 10.1002/adma.201201127 Org. Electron. Sworakowski 33 300 2016 10.1016/j.orgel.2016.03.031 Photochem. Photobiol. Liu 137 99 2000 10.1016/S1010-6030(00)00361-0 Zh. Fiz. Khim. Shcherbo 53 566 1978