Abstract
Using Cadogan or copper-catalyzed Ullmann reaction, new shape-persistent ladder oligo(p -aniline)s were synthesized from 2,7-carbazole derivatives. Physical characterization
of these electroactive and photoactive organic materials is also presented.
1 Introduction
2 Synthesis of Ladder Oligo(p -aniline)s via the Cadogan Ring-Closure Reaction
2.1 Indolocarbazole Derivatives
2.2 Diindolocarbazole Derivatives
2.3 An Approach to the Synthesis of a Tetramer
3 Synthesis of Ladder Oligo(p -aniline)s via the Copper-Catalyzed Ullmann Ring-Closure Reaction
3.1 Diindolocarbazole Derivatives
3.2 Tetramer Derivatives
4 Characterization of the Ladder Oligo(p -aniline)s
5 Conclusion
Key words
carbazoles - oligoanilines - Cadogan reaction - Ullmann reaction - ladder oligomers
References
1a </A>
Burroughes JH.
Bradley DDC.
Brown AR.
Marks RN.
Mackay K.
Friend RH.
Burns PL.
Holmes AB.
Nature
1990,
347:
539
1b </A>
Kulkarni AP.
Tonzola CJ.
Babel A.
Jenekhe SA.
Chem. Mater.
2004,
16:
4556
2a </A>
Dimitrakopoulos CD.
Malenfant PRL.
Adv. Mater.
2002,
14:
99
2b </A>
Katz HE.
Chem. Mater.
2004,
16:
4748
2c </A>
Chabinyc M.
Salleo A.
Chem. Mater.
2004,
16:
4509
3a </A>
Winder C.
Sariciftci NS.
J. Mater. Chem.
2004,
14:
1077
3b </A>
Coakley KM.
McGehee MD.
Chem. Mater.
2004,
16:
4533
4a </A>
Kelley TW.
Muyres DV.
Baude PF.
Smith TP.
Jones TD.
Mater. Res. Soc. Symp. Ser.
2003,
771:
169
4b </A>
Klauk H.
Halik M.
Zschieschang U.
Eder F.
Schmid G.
Dehm C.
Appl. Phys. Lett.
2003,
82:
4175
4c </A>
Jurchescu OD.
Baas J.
Palstra TTM.
Appl. Phys. Lett.
2004,
84:
3061
4d </A>
Sundar VC.
Zaumseil J.
Podzorov V.
Menard E.
Willett RL.
Someya T.
Gershenson ME.
Rogers JA.
Science
2004,
303:
1644
5a </A>
Horowitz G.
Garnier F.
Yassar A.
Hajlaoui R.
Kouki F.
Adv. Mater.
1996,
8:
52
5b </A>
Dimitrakopoulos CD.
Furman BK.
Graham T.
Hedge S.
Purushothaman S.
Synth. Met.
1998,
92:
47
5c </A>
Videlot C.
Ackermann J.
Blanchard P.
Raimundo JM.
Frère P.
Allain M.
Bettignies R.
Levillain E.
Roncali J.
Adv. Mater.
2003,
15:
306
5d </A>
Halik M.
Klauk H.
Zschieschang U.
Schmid G.
Ponomarenko S.
Kirchmeyer S.
Weber W.
Adv. Mater.
2003,
15:
917
6a </A>
Bao Z.
Dodabalapur A.
Lovinger AJ.
Appl. Phys. Lett.
1996,
69:
4108
6b </A>
Sirringhaus H.
Tessler N.
Friend RH.
Science
1998,
280:
1741
6c </A>
Ong BS.
Wu Y.
Liu P.
Gardner S.
J. Am. Chem. Soc.
2004,
126:
3378
<A NAME="RA37304ST-7">7 </A>
Lin Y.-Y.
Gundlach DJ.
Nelson SF.
Jackson TN.
IEEE Electron Device Lett.
1997,
18:
606
8a </A>
Laquindanum JG.
Katz HE.
Lovinger AJ.
J. Am. Chem. Soc.
1998,
120:
664
8b </A>
Katz HE.
Bao Z.
Gilat SL.
Acc. Chem. Res.
2001,
34:
359
8c </A>
Miao Q.
Nguyen T.-Q.
Someya T.
Blanchet GB.
Nuckolls C.
J. Am. Chem. Soc.
2003,
125:
10284
8d </A>
Meng H.
Zheng J.
Lovinger AJ.
Wang BC.
Patten PGV.
Bao Z.
Chem. Mater.
2003,
15:
1778
9a </A>
Curtis MD.
Cao J.
Kampf JW.
J. Am. Chem. Soc.
2004,
126:
4318
9b </A>
Mas-Torrent M.
Hadley P.
Bromley ST.
Ribas X.
Tarres J.
Mas M.
Molins E.
Veciana J.
Rovira C.
J. Am. Chem. Soc.
2004,
126:
8546
9c </A>
Moon H.
Zeis R.
Borkent E.-J.
Besnard C.
Lovinger A.
Siegrist T.
Kloc C.
Bao Z.
J. Am. Chem. Soc.
2004,
126:
15322
<A NAME="RA37304ST-10">10 </A>
Gundlach DJ.
Lin YY.
Jackson TN.
Nelson SF.
Schlom DG.
IEEE Electron Device Lett.
1997,
18:
87
11a </A>
Herwig PT.
Müllen K.
Adv. Mater.
1999,
11:
480
11b </A>
Afzali A.
Dimitrakopoulos CD.
Breen TL.
J. Am. Chem. Soc.
2002,
124:
8812
<A NAME="RA37304ST-12">12 </A>
Meng H.
Bendikov M.
Mitchell G.
Helgeson R.
Wudl F.
Bao Z.
Siegrist T.
Kloc C.
Chen C.-H.
Adv. Mater.
2003,
15:
1090
13a </A>
Anthony JE.
Brooks JS.
Eaton DL.
Parkin SR.
J. Am. Chem. Soc.
2001,
123:
9482
13b </A>
Anthony JE.
Eaton DL.
Parkin SR.
Org. Lett.
2002,
4:
15
<A NAME="RA37304ST-14">14 </A>
Sheraw CD.
Jackson TN.
Eaton DL.
Anthony JE.
Adv. Mater.
2003,
15:
2009
<A NAME="RA37304ST-15">15 </A>
Laquindanum JG.
Katz HE.
Lovinger AJ.
J. Am. Chem. Soc.
1998,
120:
664
<A NAME="RA37304ST-16">16 </A>
Payne MM.
Odom SA.
Parkin SR.
Anthony JE.
Org. Lett.
2004,
6:
3325
<A NAME="RA37304ST-17">17 </A>
Laquindanum JG.
Katz HE.
Lovinger AJ.
Dodabalapur A.
Adv. Mater.
1997,
9:
36
<A NAME="RA37304ST-18">18 </A>
Li X.-C.
Sirringhaus H.
Garnier F.
Holmes AB.
Moratti SC.
Feeder N.
Clegg W.
Teat SJ.
Friend RH.
J. Am. Chem. Soc.
1998,
120:
2206
19a </A>
Mazaki Y.
Kobayashi K.
Tetrahedron Lett.
1989,
30:
3315
19b </A>
Wex B.
Kaafarani BR.
Neckers DC.
J. Org. Chem.
2004,
69:
2197
19c </A>
Yamaguchi S.
Xu C.
Tamao K.
J. Am. Chem. Soc.
2003,
125:
13662
<A NAME="RA37304ST-20">20 </A>
Sirringhaus H.
Friend RH.
Wang C.
Leuninger J.
Müllen K.
J. Mater. Chem.
1999,
9:
2095
21a </A>
Xiao K.
Liu Y.
Huang X.
Xu Y.
Yu G.
Zhu D.
J. Phys. Chem. B
2003,
107:
9226
21b </A>
Xu G.
Bao Z.
Groves JT.
Langmuir
2002,
16:
1834
22a </A>
Carroll RL.
Gorman CB.
Angew. Chem. Int. Ed.
2002,
41:
4378
22b </A>
James DK.
Tour JM.
Chem. Mater.
2004,
16:
4423
<A NAME="RA37304ST-23">23 </A>
Cadogan JIG.
Carmeron-Wodd M.
Makie RK.
Searle RJG.
J. Chem. Soc.
1965,
4831
<A NAME="RA37304ST-24">24 </A>
Lindley J.
Tetrahedron
1984,
40:
1433
<A NAME="RA37304ST-25">25 </A>
Belletête M.
Bédard M.
Leclerc M.
Durocher G.
Synth. Met.
2004,
146:
99
26a </A>
Morin JF.
Leclerc M.
Macromolecules
2001,
34:
4680
26b </A>
Zotti G.
Schiavon G.
Zecchin S.
Morin JF.
Leclerc M.
Macromolecules
2002,
35:
2122
26c </A>
Morin JF.
Drolet N.
Tao Y.
Leclerc M.
Chem. Mater.
2004,
16:
4619
<A NAME="RA37304ST-27">27 </A>
Grotta HM.
Riggle CJ.
Bearse AE.
J. Org. Chem.
1961,
26:
1509
28a </A>
Robinson B.
J. Chem. Soc.
1963,
3097
28b </A>
Yudina LN.
Bergman J.
Tetrahedron
2003,
59:
1265
<A NAME="RA37304ST-29">29 </A>
Kistenmacher A.
Müllen K.
J. Heterocycl. Chem.
1992,
29:
1237
<A NAME="RA37304ST-30">30 </A>
Katritzky AR.
Li J.
Stevens CV.
J. Org. Chem.
1995,
60:
3401
<A NAME="RA37304ST-31">31 </A>
Wahlström N.
Stensland B.
Bergman J.
Synthesis
2004,
1187
<A NAME="RA37304ST-32">32 </A>
Black DSC.
Ivory AJ.
Kumar N.
Tetrahedron
1995,
51:
11801
<A NAME="RA37304ST-33">33 </A>
Tholander J.
Bergman J.
Tetrahedron
1999,
55:
12577
<A NAME="RA37304ST-34">34 </A>
Wakim S.
Bouchard J.
Simard M.
Drolet N.
Tao Y.
Leclerc M.
Chem. Mater.
2004,
16:
4386
<A NAME="RA37304ST-35">35 </A> To be published
<A NAME="RA37304ST-36">36 </A>
Lowinger TB.
Chu JC.
Spence PL.
Tetrahedron Lett.
1995,
36:
8383
37a </A>
Testaferri L.
Tingoli M.
Tiecco M.
Tetrahedron Lett.
1980,
21:
3099
37b </A>
Testaferri L.
Tingoli M.
Tiecco M.
J. Org. Chem.
1980,
45:
4376
37c </A>
Shaw JE.
J. Org. Chem.
1991,
56:
3728
<A NAME="RA37304ST-38">38 </A>
Testaferri L.
Tiecco M.
Tingoli M.
Chianelli D.
Montanucci M.
Synthesis
1983,
751
<A NAME="RA37304ST-39">39 </A>
Bouchard J.
Wakim S.
Leclerc M.
J. Org. Chem.
2004,
69:
5705
<A NAME="RA37304ST-40">40 </A>
Bouchard J.
Wakim S.
Leclerc M.
Synth. Commun.
2004,
34:
2737
<A NAME="RA37304ST-41">41 </A>
Cammidge AN.
Crépy KVL.
J. Org. Chem.
2003,
68:
6832
<A NAME="RA37304ST-42">42 </A>
Jackson CL.
Calhane DF.
Am. Chem. J.
1902,
28:
451
<A NAME="RA37304ST-43">43 </A>
Wakim S.
Bouchard J.
Blouin N.
Michaud A.
Leclerc M.
Org. Lett.
2004,
6:
3413
<A NAME="RA37304ST-44">44 </A>
Bellamy FD.
Ou K.
Tetrahedron Lett.
1984,
25:
839
45a </A>
Driver MS.
Hartwig JF.
J. Am. Chem. Soc.
1996,
118:
7217
45b </A>
Hartwig JF.
Kawatsura M.
Hauck SI.
Shaughnessy KH.
Alcazar-Roman LM.
J. Org. Chem.
1999,
64:
5575
45c </A>
Mann G.
Hartwig JF.
Driver MS.
Fernandez-Rivas C.
J. Am. Chem. Soc.
1998,
120:
827
46a </A>
Wolfe JP.
Wagaw S.
Buchwald SL.
J. Am. Chem. Soc.
1996,
118:
7215
46b </A>
Ali MH.
Buchwald SL.
J. Org. Chem.
2001,
66:
2560
<A NAME="RA37304ST-47">47 </A>
Lin G.
Zhang A.
Tetrahedron
2000,
56:
7163
48a </A>
Lindley J.
Tetrahedron
1984,
40:
1433
48b </A>
Hassan J.
Sévignon M.
Gozzi C.
Schulz E.
Lemaire M.
Chem. Rev.
2002,
102:
1359
48c </A>
Ley S.
Thomas AW.
Angew. Chem. Int. Ed.
2003,
43:
5400
<A NAME="RA37304ST-49">49 </A>
Field JE.
Hill TJ.
Venkataraman D.
J. Org. Chem.
2003,
68:
6071
<A NAME="RA37304ST-50">50 </A>
1 H NMR (400 MHz, THF-d
8 ): δ = 9.98 (s, 2 H, NH), 8.29 (d, 2 H, J = 2.0 Hz), 8.20 (s, 2 H), 8.15 (s, 2 H), 8.05 (s, 2 H), 7.46 (dd, 2 H, J = 8.5, 2.0 Hz), 7.40 (d, 2 H, J = 8.6 Hz), 4.50 (t, 4 H, J = 7.2 Hz), 1.97 (m, 4 H), 1.40 (3 m, 20 H), 0.86 (t, 6 H, J = 6.8 Hz). HRMS: m/z calcd for C46 H48 N4 Br2 : 814.2245; found: 814.2227.
<A NAME="RA37304ST-51">51 </A>
Paine AJ.
J. Am. Chem. Soc.
1987,
109:
1496
<A NAME="RA37304ST-52">52 </A>
Belletête M.
Durocher G.
Hamel S.
Côté M.
Wakim S.
Leclerc M.
J. Chem. Phys.
2005,
122:
104303
<A NAME="RA37304ST-53">53 </A>
Becker RS.
Theory and Interpretations of Fluorescence and Phosphorescence
John Wiley and Sons;
New York:
1969.
<A NAME="RA37304ST-54">54 </A>
Wu Y.
Li Y.
Gardner S.
Ong BS.
J. Am. Chem. Soc.
2005,
127:
614
