What About the Five-Membered Ring? Cyclopenta-fused Polycyclic Aromatic Hydrocarbons as a Building Block for Functional Materials

Kyle N. Plunkett

doi:10.1055/s-0032-1318434

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(8): 898-902
DOI: 10.1055/s-0032-1318434

synpacts

What About the Five-Membered Ring? Cyclopenta-fused Polycyclic Aromatic Hydrocarbons as a Building Block for Functional Materials

Autor*innen

Kyle N. Plunkett*

Department of Chemistry and Biochemistry, Southern Illinois University, 1245 Lincoln Drive, Carbondale, IL 62901, USA Fax: +1(618)4536408 eMail: kplunkett@chem.siu.edu

Abstract

Alle Artikel dieser Rubrik

Dedicated to Rhett Emmett.

Abstract

There has been recent interest in creating new functional materials based on cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAH) that can be integrated into organic electronic devices. These five-membered-ring-containing materials are appealing because the electronic properties that are associated with their nonalternate PAH ring structure are not typically accessible by alternate PAH composed solely of six-membered rings. This paper highlights some recent synthetic advances for new CP-PAH systems and describes work from our lab that we believe has helped advance the methodology to create new CP-PAH-containing small molecules and polymeric materials.

Key words

cyclopenta-fused polycyclic aromatic hydrocarbons - cross-coupling - electron acceptors - donor–acceptor copolymer - organic electronic materials

Volltext

Referenzen

References and Notes
1 Clar E. Polycyclic Hydrocarbons . Academic Press; New York: 1964
2 Diederich F, Rubin Y. Angew. Chem., Int. Ed. Engl. 1992; 31: 1101
3 Trost BM, Bright GM. J. Am. Chem. Soc. 1967; 89: 4244
4 Trost BM, Bright GM, Frihart C, Brittelli D. J. Am. Chem. Soc. 1971; 93: 737
5 Diogo HP, Kiyobayashi T, Minas da Piedade ME, Burlak N, Rogers DW, McMasters D, Persy G, Wirz J, Liebman JF. J. Am. Chem. Soc. 2002; 124: 2065
6 Barth WE, Lawton RG. J. Am. Chem. Soc. 1966; 88: 380
7 Fragments of Fullerenes and Carbon Nanotubes . Petrukhina MA, Scott LT. John Wiley and Sons; Hoboken: 2012
8 To say five-membered-ring systems have not been utilized for material design would be short-sighted. However, most of these systems utilize the five-membered ring to simply planarize neighboring benzene rings for greater π-overlap between aromatic segments of a molecule (i.e., fluorene).
9 Scott LT, Hashemi MM, Bratcher MS. J. Am. Chem. Soc. 1992; 114: 1920
10 Scott LT, Hashemi MM, Meyer DT, Warren HB. J. Am. Chem. Soc. 1991; 113: 7082
11 Butterfield AM, Gilomen B, Siegel JS. Org. Process Res. Dev. 2012; 16: 664
12 Thompson BC, Fréchet JM. J. Angew. Chem. Int. Ed. 2008; 47: 58
13 Xie Q, Arias F, Echegoyen L. J. Am. Chem. Soc. 1993; 115: 9818
14 Reed CA, Bolskar RD. Chem. Rev. 2000; 100: 1075
15 Gong X, Tong M, Brunetti FG, Seo J, Sun Y, Moses D, Wudl F, Heeger AJ. Adv. Mater. 2011; 23: 2272
16 Smet M, Shukla R, Fülöp L, Dehaen W. Eur. J. Org. Chem. 1998; 2769
17 Dang H, Garcia-Garibay MA. J. Am. Chem. Soc. 2001; 123: 355
18 Dang H, Levitus M, Garcia-Garibay MA. J. Am. Chem. Soc. 2002; 124: 136
19 Wegner HA, Scott LT, De Meijere A. J. Org. Chem. 2003; 68: 883
20 Eversloh LC, Avlasevich Y, Li C, Müllen K. Chem. Eur. J. 2011; 17: 12756
21 Xia H, Liu D, Xu X, Miao Q. Chem. Commun. 2013; 49: 4301
22 Brunetti FG, Gong X, Tong M, Heeger AJ, Wudl F. Angew. Chem. Int. Ed. 2010; 49: 532
23 Brunetti FG, Varotto A, Batara NA, Wudl F. Chem. Eur. J. 2011; 17: 8604
24 Chase DT, Rose BD, McClintock SP, Zakharov LN, Haley MM. Angew. Chem. Int. Ed. 2011; 50: 1127
25 Chase DT, Fix AG, Rose BD, Weber CD, Nobusue S, Stockwell CE, Zakharov LN, Lonergan MC, Haley MM. Angew. Chem. Int. Ed. 2011; 50: 11103
26 Shimizu A, Tobe Y. Angew. Chem. Int. Ed. 2011; 50: 6906
27 Reisch H, Wiesler U, Scherf U, Tuytuylkov N. Macromolecules 1996; 29: 8204
28 Zhang Q, Kawasumi K, Segawa Y, Itami K, Scott LT. J. Am. Chem. Soc. 2012; 134: 15664
29 Eliseeva MN, Scott LT. J. Am. Chem. Soc. 2012; 134: 15169
30 Kawase T, Konishi A, Hirao Y, Matsumoto K, Kurata H, Kubo T. Chem. Eur. J. 2009; 15: 2653
31 Saito M, Nakamura M, Tajima T. Chem. Eur. J. 2008; 14: 6062
32 Rivera-Fuentes P, Rekowski Mvon W, Schweizer WB, Gisselbrecht J.-P, Boudon C, Diederich F. Org. Lett. 2012; 14: 4066
33 Cao H, Van Ornum SG, Deschamps J, Flippen-Anderson J, Laib F, Cook JM. J. Am. Chem. Soc. 2005; 127: 933
34 Mohebbi AR, Wudl F. Chem. Eur. J. 2011; 17: 2642
35 Mohebbi AR, Yuen J, Fan J, Munoz C, Wang MF, Shirazi RS, Seifter J, Wudl F. Adv. Mater. 2011; 23: 4644
36 Wang M, Mohebbi AR, Sun Y, Wudl F. Angew. Chem. Int. Ed. 2012; 51: 6920
37 Chase DT, Fix AG, Kang SJ, Rose BD, Weber CD, Zhong Y, Zakharov LN, Lonergan MC, Nuckolls C, Haley MM. J. Am. Chem. Soc. 2012; 134: 10349
38 Meijer EJ, De Leeuw DM, Setayesh S, Veenendaal EV, Huisman B.-H, Blom PW. M, Hummelen JC, Scherf U, Klapwijk TM. Nature Mater. 2003; 2: 678
39 Wood JD, Jellison JL, Finke AD, Wang L, Plunkett KN. J. Am. Chem. Soc. 2012; 134: 15783
40 Lee C.-H, Plunkett KN. Org. Lett. 2013; DOI 10.1021/o1400093g
41 Jellison JL, Lee C.-H, Zhu X, Wood JD, Plunkett KN. Angew. Chem. Int. Ed. 2012; 51: 12321 ; Angew. Chem. 2012, 124, 12487
42 Garcia–Garibay has previously prepared the single five-membered ring containing aceanthrylen-2-yltrimethylsilane
43 Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
44 Cho J.-Y, Tse MK, Holmes D, Maleczka RE, Smith MR. Science 2002; 295: 305
45 Coventry DN, Batsanov AS, Goeta AE, Howard JA. K, Marder TB, Perutz RN. Chem. Commun. 2005; 2172
46 Plunkett KN, Godula K, Nuckolls C, Tremblay N, Whalley AC, Xiao S. Org. Lett. 2009; 11: 2225
47 Mondal R, Ko S, Norton JE, Miyaki N, Becerril HA, Verploegen E, Toney MF, Brédas J.-L, McGehee MD, Bao Z. J. Mater. Chem. 2009; 19: 7195