Abstract
Oligo-p -phenylenes have proven to be versatile building blocks for the generation of self-assembled
nanoaggregates with interesting optical properties via vapor deposition on solid supports.
Preliminary studies have shown that both the properties and the morphologies of these
aggregates can be influenced by the introduction of functional groups. To this end,
we have developed general approaches to the synthesis of symmetrically and unsymmetrically
1,4′′′-substituted p -quaterphenylenes through the application of a reliable Suzuki cross-coupling strategy.
Key words
cross-coupling reaction - oligo-p -phenylenes - rod-like molecules - Suzuki
References
<A NAME="RZ22906SS-1A">1a </A>
Müllen K.
Wegner G.
Electronic Materials: The Oligomer Approach
Wiley-VCH;
Weinheim:
1998.
<A NAME="RZ22906SS-1B">1b </A>
Fichou D.
Handbook of Oligo- and Polythiophenes
Wiley-VCH;
Weinheim:
1999.
<A NAME="RZ22906SS-1C">1c </A>
Nalva HS.
Handbook of Advanced Electronic and Photonic Materials and Devices
Academic Press;
San Diego:
2000.
<A NAME="RZ22906SS-1D">1d </A>
Müllen K.
Scherf U.
Organic Light Emitting Devices - Synthesis, Properties and Applications
Wiley-VCH;
Weinheim:
2006.
<A NAME="RZ22906SS-1E">1e </A>
Klauk H.
Organic Electronics - An Industrial Perspective
Wiley-VCH;
Weinheim:
2006.
<A NAME="RZ22906SS-2A">2a </A>
Schwab PFH.
Levin MD.
Michl J.
Chem. Rev.
1999,
99:
1863
<A NAME="RZ22906SS-2B">2b </A>
Schwab PFH.
Smith JR.
Michl J.
Chem. Rev.
2005,
105:
1197
<A NAME="RZ22906SS-3">3 </A>
Ziegler G. In Handbook of Organic Conductive Molecules and Polymers
Vol. 3:
Nalwa HS.
Wiley;
New York:
1997.
Chap. 13.
<A NAME="RZ22906SS-4A">4a </A>
Krause B.
Dürr AC.
Ritley K.
Schreiber F.
Dosch H.
Smilgies D.
Phys. Rev. B: Condens. Matter Mater. Phys.
2002,
66:
235404
<A NAME="RZ22906SS-4B">4b </A>
Würthner F.
Chem. Commun.
2004,
1564
<A NAME="RZ22906SS-5">5 </A>
Bendikov M.
Wudl F.
Perepichka DF.
Chem. Rev.
2004,
104:
4891
<A NAME="RZ22906SS-6">6 </A>
James DK.
Tour JM.
Top. Curr. Chem.
2005,
257:
33
<A NAME="RZ22906SS-7A">7a </A>
Resel R.
Thin Solid Films
2003,
433:
1
<A NAME="RZ22906SS-7B">7b </A>
Balzer F.
Rubahn H.-G.
Adv. Funct. Mater.
2005,
14:
17
<A NAME="RZ22906SS-7C">7c </A>
Balzer F.
Rubahn H.-G.
Phys. Unserer Zeit
2005,
36:
36
<A NAME="RZ22906SS-8A">8a </A>
Witte G.
Woell C.
J. Mater. Res.
2004,
19:
1889
<A NAME="RZ22906SS-8B">8b </A>
Hertel D.
Müller CD.
Meerholz K.
Chem. Unserer Zeit
2005,
39:
336
<A NAME="RZ22906SS-9A">9a </A>
Balzer F.
Rubahn H.-G.
Appl. Phys. Lett.
2001,
79:
2860
<A NAME="RZ22906SS-9B">9b </A>
Balzer F.
Rubahn H.-G.
Surf. Sci.
2002,
507:
588
<A NAME="RZ22906SS-10">10 </A>
Yanagi H.
Morikawa T.
Appl. Phys. Lett.
1999,
75:
187
<A NAME="RZ22906SS-11A">11a </A>
Balzer F.
Bordo VG.
Simonsen AC.
Rubahn H.-G.
Appl. Phys. Lett.
2003,
82:
10
<A NAME="RZ22906SS-11B">11b </A>
Balzer F.
Bordo VG.
Simonsen AC.
Rubahn H.-G.
Phys. Rev. B: Condens. Matter Mater. Phys.
2003,
67:
115408
<A NAME="RZ22906SS-12A">12a </A>
Quochi F.
Cordella F.
Orrì R.
Communal JE.
Verzeroli P.
Mura A.
Bongiovanni G.
Andreev A.
Sitter H.
Sariciftci NS.
Appl. Phys. Lett.
2004,
84:
4454
<A NAME="RZ22906SS-12B">12b </A>
Quochi F.
Cordella F.
Mura A.
Bongiovanni G.
Balzer F.
Rubahn H.-G.
J. Phys. Chem. B
2005,
109:
21690
<A NAME="RZ22906SS-12C">12c </A>
Quochi F.
Cordella F.
Mura A.
Bongiovanni G.
Balzer F.
Rubahn H.-G.
Appl. Phys. Lett.
2006,
88:
041106
<A NAME="RZ22906SS-13">13 </A>
Kjelstrup-Hansen J.
Henrichsen HH.
Bøggild P.
Rubahn H.-G.
Thin Solid Films
2006,
515:
827
<A NAME="RZ22906SS-14">14 </A>
Henrichsen HH.
Kjelstrup-Hansen J.
Engstroem D.
Clausen CH.
Bøggild P.
Rubahn H.-G.
Appl. Phys. A
2006, submitted
<A NAME="RZ22906SS-15">15 </A>
Kjelstrup-Hansen J.
Bøggild P.
Rubahn H.-G.
J. Phys. C
2006, submitted
<A NAME="RZ22906SS-16A">16a </A>
Schiek M.
Lützen A.
Koch R.
Al-Shamery K.
Balzer F.
Frese R.
Rubahn H.-G.
Appl. Phys. Lett.
2005,
86:
153107
<A NAME="RZ22906SS-16B">16b </A>
Schiek M.
Lützen A.
Al-Shamery K.
Balzer F.
Rubahn H.-G.
Surf. Sci.
2006,
600:
4030
<A NAME="RZ22906SS-16C">16c </A>
Schiek M.
Lützen A.
Al-Shamery K.
Balzer F.
Rubahn H.-G.
Cryst. Growth Des.
2006, accepted for publication
<A NAME="RZ22906SS-17">17 </A>
Brewer J.
Schiek M.
Lützen A.
Al-Shamery K.
Rubahn H.-G.
Nano Lett.
2006,
6:
2656
<A NAME="RZ22906SS-18">18 </A>
Schmidt H.
Schultz G.
Justus Liebigs Ann. Chem.
1880,
203:
129
<A NAME="RZ22906SS-19A">19a </A>
Scheinbaum ML.
J. Chem. Soc., Chem. Commun.
1969,
1235
<A NAME="RZ22906SS-19B">19b </A>
Pavlopoulos TG.
Hammond PR.
J. Am. Chem. Soc.
1974,
96:
6568
<A NAME="RZ22906SS-20A">20a </A>
Keegstra MA.
De Feyter S.
De Schryver FC.
Müllen K.
Angew. Chem., Int. Ed. Engl.
1996,
35:
774 ; Angew. Chem. 1996 , 108 , 830
<A NAME="RZ22906SS-20B">20b </A>
Iyer VS.
Wehmeier M.
Brand JD.
Keegstra MA.
Müllen K.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1604 ; Angew. Chem. 1997 , 109 , 1676
<A NAME="RZ22906SS-20C">20c </A>
Müller M.
Iyer VS.
Kübel C.
Enkelmann V.
Müllen K.
Angew. Chem., Int. Ed. Engl.
1997,
36:
1607 ; Angew. Chem . 1997 , 109 , 1679
<A NAME="RZ22906SS-20D">20d </A>
Fechtenkötter A.
Saalwächter K.
Harbison MA.
Müllen K.
Spiess HW.
Angew. Chem. Int. Ed.
1999,
38:
3039 ; Angew. Chem . 1999 , 111 , 3224
<A NAME="RZ22906SS-20E">20e </A>
Ito S.
Herwig PT.
Böhme T.
Rabe JP.
Rettig W.
Müllen K.
J. Am. Chem. Soc.
2000,
122:
7698
<A NAME="RZ22906SS-21A">21a </A>
Stille JK.
Rakutis RO.
Mukamal H.
Harris FW.
Macromolecules
1968,
1:
431
<A NAME="RZ22906SS-21B">21b </A>
Morgenroth F.
Reuther E.
Müllen K.
Angew. Chem., Int. Ed. Engl.
1997,
36:
631 ; Angew. Chem . 1997 , 109 , 647
<A NAME="RZ22906SS-21C">21c </A>
Wiesler U.-M.
Müllen K.
Chem. Commun.
1999,
2293
<A NAME="RZ22906SS-21D">21d </A>
Dötz F.
Brand JD.
Ito S.
Gherghel L.
Müllen K.
J. Am. Chem. Soc.
2000,
122:
7707
<A NAME="RZ22906SS-21E">21e </A>
Wiesler U.-M.
Berresheim AJ.
Morgenroth F.
Lieser G.
Müllen K.
Macromolecules
2001,
34:
187
<A NAME="RZ22906SS-21F">21f </A>
Weil T.
Wiesler U.-M.
Herrmann A.
Bauer R.
Hofkens J.
De Schryver FC.
Müllen K.
J. Am. Chem. Soc.
2001,
123:
8101
<A NAME="RZ22906SS-21G">21g </A>
Simpson CD.
Brand JD.
Berresheim AJ.
Przybilla L.
Räder HJ.
Müllen K.
Chem. Eur. J.
2002,
8:
1424
<A NAME="RZ22906SS-22">22 </A>
Subramaniam G.
Gilpin RK.
Synthesis
1992,
1232
<A NAME="RZ22906SS-23A">23a </A>
Hart H.
Harada K.
Tetrahedron Lett.
1985,
26:
29
<A NAME="RZ22906SS-23B">23b </A>
Hart H.
Harada K.
Frank Du C.-J.
J. Org. Chem.
1985,
50:
3104
<A NAME="RZ22906SS-23C">23c </A>
Harada K.
Hart H.
Frank Du C.-J.
J. Org. Chem.
1985,
50:
5524
<A NAME="RZ22906SS-23D">23d </A>
Frank Du C.-J.
Hart H.
Ng K.-KD.
J. Org. Chem.
1986,
51:
3162
<A NAME="RZ22906SS-24A">24a </A>
Rebmann A.
Zhou J.
Schuler P.
Stegmann HB.
Rieker A.
J. Chem. Res., Synop.
1996,
318
<A NAME="RZ22906SS-24B">24b </A>
Rebmann A.
Zhou J.
Schuler P.
Rieker A.
Stegmann HB.
J. Chem. Soc., Perkin Trans. 2
1997,
1615
<A NAME="RZ22906SS-25">25 </A>
Harley-Mason J.
Mann FG.
J. Chem. Soc.
1940,
1379
<A NAME="RZ22906SS-26A">26a </A>
Metal-catalyzed Cross-Coupling Reactions
2nd ed.:
de Meijere A.
Diederich F.
Wiley-VCH;
Weinheim:
2004.
<A NAME="RZ22906SS-26B">26b </A>
Lie JJ.
Gribble GW.
Palladium in Heterocyclic Chemistry
Pergamon Press, Elsevier;
Amsterdam:
2000.
<A NAME="RZ22906SS-26C">26c </A>
Cross-Coupling Reactions
Miyaura N.
Springer;
Berlin:
2002.
<A NAME="RZ22906SS-26D">26d </A> For a special issue on cross-coupling reactions, see:
Tamao K.
Hiyama T.
Negishi E.
J. Organomet. Chem.
2002,
653:
1
For examples of the application of nickel-catalyzed Kharash couplings for the synthesis
of oligo-p -phenylenes, see:
<A NAME="RZ22906SS-27A">27a </A>
Saitoh H.
Saito K.
Yamamura Y.
Matsuyama H.
Kikuchi K.
Iyoda M.
Ikemoto I.
Bull. Chem. Soc. Jpn.
1993,
66:
2847
<A NAME="RZ22906SS-27B">27b </A>
Ung VA.
Bardwell DA.
Jeffery JC.
Maher JP.
McCleverty JA.
Ward MD.
Williamson A.
Inorg. Chem.
1996,
35:
5290
<A NAME="RZ22906SS-27C">27c </A>
Abdul-Rahman A.
Amoroso AA.
Branston TN.
Das A.
Maher JP.
McCleverty JA.
Ward MD.
Wlodarczyk A.
Polyhedron
1997,
16:
4353
For examples of the application of palladium-catalyzed Kharash couplings for the synthesis
of oligo-p -phenylenes, see:
<A NAME="RZ22906SS-28A">28a </A>
Kallitsis JK.
Kakali F.
Gravalos KG.
Macromolecules
1994,
27:
4509
<A NAME="RZ22906SS-28B">28b </A>
Kallitsis JK.
Gravalos KG.
Hilberer A.
Hadziioannou G.
Macromolecules
1997,
30:
2989
<A NAME="RZ22906SS-28C">28c </A>
Kauffmann JM.
Synthesis
1999,
918
<A NAME="RZ22906SS-28D">28d </A>
Rathore R.
Burns CL.
Deselnicu MI.
Org. Lett.
2001,
3:
2887
For examples of the application of palladium-catalyzed Suzuki couplings for the synthesis
of oligo-p -phenylenes, see:
<A NAME="RZ22906SS-29A">29a </A>
Liess P.
Hensel V.
Schlüter A.-D.
Liebigs Ann.
1996,
1037
<A NAME="RZ22906SS-29B">29b </A>
Fran J.
Karakaya B.
Schäfer A.
Schlüter AD.
Tetrahedron
1997,
53:
15459
<A NAME="RZ22906SS-29C">29c </A>
Hensel V.
Schlüter A.-D.
Chem. Eur. J.
1999,
5:
421
<A NAME="RZ22906SS-29D">29d </A>
Sakai N.
Brennan KC.
Weiss LA.
Matile S.
J. Am. Chem. Soc.
1997,
119:
8726
<A NAME="RZ22906SS-29E">29e </A>
Ghebremariam B.
Matile S.
Tetrahedron Lett.
1998,
39:
5335
<A NAME="RZ22906SS-29F">29f </A>
Ghebremariam B.
Sidorov V.
Matile S.
Tetrahedron Lett.
1999,
40:
1445
<A NAME="RZ22906SS-29G">29g </A>
Winum J.-Y.
Matile S.
J. Am. Chem. Soc.
1999,
121:
7961
<A NAME="RZ22906SS-29H">29h </A>
Robert F.
Winum J.-Y.
Sakai N.
Gerard D.
Matile S.
Org. Lett.
2000,
2:
37
<A NAME="RZ22906SS-29I">29i </A>
Sakai N.
Gerard D.
Matile S.
J. Am. Chem. Soc.
2001,
123:
2517
<A NAME="RZ22906SS-29J">29j </A>
Sakai N.
Matile S.
J. Am. Chem. Soc.
2002,
124:
1184
<A NAME="RZ22906SS-29K">29k </A>
Galda P.
Rehahn M.
Synthesis
1996,
614
<A NAME="RZ22906SS-29L">29l </A>
Kim S.
Jackiw J.
Robinson E.
Schanze KS.
Reynolds JR.
Macromolecules
1998,
31:
964
<A NAME="RZ22906SS-29M">29m </A>
Goldfinger MB.
Crawford KB.
Swager TM.
J. Org. Chem.
1998,
63:
1676
<A NAME="RZ22906SS-29N">29n </A>
Konstandakopoulou FD.
Gravalos KG.
Kallitsis JK.
Macromolecules
1998,
31:
5264
<A NAME="RZ22906SS-29O">29o </A>
Morikawa A.
Macromolecules
1998,
31:
5999
<A NAME="RZ22906SS-29P">29p </A>
Schlicke B.
Belser P.
De Cola L.
Sabbioni E.
Balzani V.
J. Am. Chem. Soc.
1999,
121:
4207
<A NAME="RZ22906SS-29Q">29q </A>
Taylor PN.
O’Connell MJ.
McNeill LA.
Hall MJ.
Alpin RT.
Anderson HL.
Angew. Chem. Int. Ed.
2000,
39:
3456 ; Angew. Chem . 2000 , 112 , 3598
<A NAME="RZ22906SS-29R">29r </A>
Read MW.
Escobedo JO.
Willis DM.
Beck PA.
Strongin RM.
Org. Lett.
2000,
2:
3201
<A NAME="RZ22906SS-29S">29s </A>
Hwang S.-W.
Chen Y.
Macromolecules
2001,
34:
2981
<A NAME="RZ22906SS-29T">29t </A>
Park J.-W.
Ediger MD.
Green MM.
J. Am. Chem. Soc.
2001,
123:
49
<A NAME="RZ22906SS-29U">29u </A>
Deng X.
Mayeux A.
Cai C.
J. Org. Chem.
2002,
67:
5279
<A NAME="RZ22906SS-29V">29v </A>
Lightowler S.
Hird M.
Chem. Mater.
2004,
16:
3963
<A NAME="RZ22906SS-29W">29w </A>
Lightowler S.
Hird M.
Chem. Mater.
2005,
27:
5538
<A NAME="RZ22906SS-30A">30a </A>
Percec V.
Okita S.
J. Polym. Sci., Part A: Polym. Chem.
1993,
31:
877
<A NAME="RZ22906SS-30B">30b </A>
Morikawa A.
Macromolecules
1998,
31:
5999
<A NAME="RZ22906SS-30C">30c </A>
Li ZH.
Wong MS.
Tao Y.
D’Iorio M.
J. Org. Chem.
2004,
69:
921
<A NAME="RZ22906SS-30D">30d </A>
Lee M.
Jang C.-J.
Ryu J.-H.
J. Am. Chem. Soc.
2004,
126:
8082
<A NAME="RZ22906SS-30E">30e </A>
Ryu J.-H.
Jang C.-J.
Yoo Y.-S.
Lim S.-G.
Lee M.
J. Org. Chem.
2005,
70:
8956
<A NAME="RZ22906SS-30F">30f </A>
Welter S.
Salluce N.
Benetti A.
Rot N.
Belser P.
Sonar P.
Grimsdale AC.
Müllen K.
Lutz M.
Spek AL.
de Cola L.
Inorg. Chem.
2005,
44:
4706
<A NAME="RZ22906SS-31">31 </A>
Broutin PE.
Cerna I.
Campaniello M.
Leroux F.
Colobert F.
Org. Lett.
2004,
6:
4419
<A NAME="RZ22906SS-32A">32a </A>
Thiemann F.
Piehler T.
Haase D.
Saak W.
Lützen A.
Eur. J. Org. Chem.
2005,
1991
<A NAME="RZ22906SS-32B">32b </A>
Pushechnikov O.
Ivonin SP.
Chaikovskaya AA.
Kudrya TN.
Pirozhenko VV.
Tolmachev AA.
Chem. Heterocycl. Compd.
1999,
35:
1313 ; without synthetic details or characterization
In fact this compound is commercially available and its synthesis has been previously
described using different approaches, see:
<A NAME="RZ22906SS-33A">33a </A>
Han Y.
Walker SD.
Young RN.
Tetrahedron Lett.
1996,
37:
2703
<A NAME="RZ22906SS-33B">33b </A>
Spivey AC.
Diaper CM.
Rudge AJ.
Chem. Commun.
1999,
835
<A NAME="RZ22906SS-33C">33c </A>
Spivey AC.
Diaper CM.
Adams H.
Rudge AJ.
J. Org. Chem.
2000,
65:
5253
<A NAME="RZ22906SS-33D">33d </A>
Sinclair DJ.
Sherburn MS.
J. Org. Chem.
2005,
70:
3730 . However, no NMR or MS data were provided
<A NAME="RZ22906SS-34">34 </A>
In fact this compound is commercially available and its synthesis has been previously
described using a different approach, see ref. 33a. However, no NMR or MS data were
provided.
This compound has been previously synthesized using a different approach, see:
<A NAME="RZ22906SS-35A">35a </A>
Pummerer R.
Sellsberger L.
Ber. Dtsch. Chem. Ges. B.
1931,
64:
2477
<A NAME="RZ22906SS-35B">35b </A>
McNamara JM.
Gleason WB.
J. Org. Chem.
1976,
41:
1071 . However, no NMR or MS data were provided
This compound is commercially available and its synthesis has been previously described
using different approaches, see:
<A NAME="RZ22906SS-36A">36a </A>
Sedov AM.
Sergeeva AA.
Novikov AN.
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol.
1970,
13:
591 ; Chem. Abstr . 1970, 73 , 87559
<A NAME="RZ22906SS-36B">36b </A>
Rottaelander M.
Palmer N.
Knochel P.
Synlett
1996,
573
<A NAME="RZ22906SS-36C">36c </A>
Sinclair DJ.
Sherburn MS.
J. Org. Chem.
2005,
70:
3730. However, no NMR or MS data were provided
This compound has been previously synthesized using a different approach, see:
<A NAME="RZ22906SS-37A">37a </A>
Theilacker W.
Schmid W.
Chem. Ber.
1951,
84:
204
<A NAME="RZ22906SS-37B">37b </A>
Theilacker W.
Berger W.
Popper P.
Chem. Ber.
1956,
89:
970. However, no NMR or MS data were provided
<A NAME="RZ22906SS-38">38 </A> This compound has been previously synthesized using a different approach, see:
Amatore C.
Jutand A.
Negre S.
Fauvarque JF.
J. Organomet. Chem.
1990,
390:
389
<A NAME="RZ22906SS-39">39 </A> This compound has been previously synthesized using a different approach, see:
Novikov AN.
Khalimova TA.
Zh. Vses. Khim. O-va. im. D. I. Mendeleeva
1962,
7:
698 ; Chem. Abstr. 1962 , 58 , 66196. However, no NMR or MS data were provided
<A NAME="RZ22906SS-40">40 </A> This compound has been previously synthesized using a different approach, see
ref. 25, 27b and 27c. See also:
Ronlan A.
Coleman J.
Hammerich O.
Parker VD.
J. Am. Chem. Soc.
1974,
96:
845
This compound has been previously synthesized using a different approach though no
spectroscopical data were given, see ref. 30a and:
<A NAME="RZ22906SS-41A">41a </A>
Jutand A.
Mosleh A.
Synlett
1993,
568
<A NAME="RZ22906SS-41B">41b </A>
Jutand A.
Mosleh A.
J. Org. Chem.
1997,
62:
261
<A NAME="RZ22906SS-42">42 </A> The formation of this compound has been postulated as an undesired by-product
in the synthesis of triarylmethane dyes; however, no analytical or structural data
was given, see:
Theilacker W.
Berger W.
Popper P.
Chem. Ber.
1956,
89:
970