title: Synthesis and Properties of Fully-Conjugated Indacenedithiophenes.
abstract: The synthesis and characterization of four fully-conjugated indacenedithiophenes (IDTs) are disclosed. In contrast to anthradithiophenes, regioselective synthesis of bothsynandantiisomers is readily achieved. Thiophene fusion imparts increased paratropic character on the central indacene core as predicted by DFT calculations and confirmed by1H NMR spectroscopy. IDTs exhibit red-shifted absorbance maxima with respect to their all-carbon analogues and undergo two-electron reduction and one-electron oxidation.
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Brian S
authors.initials: BS
authors.lastname: Young
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Daniel T
authors.initials: DT
authors.lastname: Chase
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Marshall
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Chris L
authors.initials: CL
authors.lastname: Vonnegut
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.affiliation: Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253, USA.
authors.forename: Michael M
authors.initials: MM
authors.lastname: Haley
references.citation: J Am Chem Soc. 2008 Mar 5;130(9):2706-7
references.pmid: 18260664
references.citation: Chemistry. 2009 Mar 2;15(11):2653-61
references.pmid: 19185043
references.citation: Adv Mater. 2011 Oct 11;23(38):4347-70
references.pmid: 21842474
references.citation: J Am Chem Soc. 2012 Jun 27;134(25):10349-52
references.pmid: 22697518
references.citation: J Am Chem Soc. 2012 Sep 26;134(38):15783-9
references.pmid: 22938098
references.citation: J Am Chem Soc. 2010 Aug 25;132(33):11437-9
references.pmid: 20677750
references.citation: Org Lett. 2012 Jul 20;14(14):3660-3
references.pmid: 22746993
references.citation: Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6076-9
references.pmid: 23630025
references.citation: Chemistry. 2011 Nov 4;17(45):12756-62
references.pmid: 21956345
references.citation: Angew Chem Int Ed Engl. 2008;47(3):452-83
references.pmid: 18046697
references.citation: J Am Chem Soc. 2009 Mar 4;131(8):2796-7
references.pmid: 19199434
references.citation: Photochem Photobiol Sci. 2008 Dec;7(12):1463-8
references.pmid: 19037498
references.citation: J Am Chem Soc. 2009 Apr 22;131(15):5586-608
references.pmid: 19331320
references.citation: Angew Chem Int Ed Engl. 2011 Nov 18;50(47):11103-6
references.pmid: 21953794
references.citation: Chemistry. 2012 Jul 16;18(29):8964-70
references.pmid: 22692844
references.citation: Chemistry. 2011 Feb 25;17(9):2642-6
references.pmid: 21264966
references.citation: Org Lett. 2006 Oct 26;8(22):5033-6
references.pmid: 17048836
references.citation: Chem Rev. 2007 Mar;107(3):718-47
references.pmid: 17291049
references.citation: Angew Chem Int Ed Engl. 2011 Feb 1;50(5):1127-30
references.pmid: 21268210
references.citation: J Am Chem Soc. 2008 Jul 9;130(27):8580-1
references.pmid: 18543911
references.citation: Org Lett. 2012 Aug 17;14(16):4062-5
references.pmid: 22845870
references.citation: Org Lett. 2013 Mar 15;15(6):1362-5
references.pmid: 23461389
references.citation: Chem Rev. 2004 Nov;104(11):4891-946
references.pmid: 15535637
references.citation: Chem Commun (Camb). 2011 Jul 21;47(27):7617-9
references.pmid: 21660352
references.citation: Chem Rev. 2006 Dec;106(12):5028-48
references.pmid: 17165682
references.citation: Adv Mater. 2011 Oct 25;23(40):4644-8
references.pmid: 21953746
references.citation: Org Lett. 2013 Sep 20;15(18):4782-5
references.pmid: 23980895
references.citation: Adv Mater. 2010 Sep 8;22(34):3876-92
references.pmid: 20715063
references.citation: J Am Chem Soc. 2008 Dec 3;130(48):16274-86
references.pmid: 19006312
references.citation: Org Lett. 2004 Sep 16;6(19):3325-8
references.pmid: 15355043
references.citation: J Am Chem Soc. 2005 Apr 13;127(14):4986-7
references.pmid: 15810810
references.citation: Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6906-10
references.pmid: 21678534
references.citation: Bioorg Med Chem Lett. 2012 Aug 15;22(16):5322-5
references.pmid: 22796181
references.citation: Chem Soc Rev. 2012 Dec 7;41(23):7857-89
references.pmid: 22918297