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2017 | Supplement | Chapter

Nanographenes and Graphene Nanoribbons with Zigzag-Edged Structures

Authors : Junzhi Liu, Reinhard Berger, Klaus Müllen, Xinliang Feng

Published in: From Polyphenylenes to Nanographenes and Graphene Nanoribbons

Publisher: Springer International Publishing

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Abstract

Compared with armchair-edged nanographenes (NGs) and graphene nanoribbons (GNRs), graphene nanostructures with zigzag edge peripheries display unique electronic, magnetic, and photophysical properties resulting from the spin-polarized state at the zigzag edges. More interestingly, some possess prominent biradical/polyradical character in the ground state. Thanks to the development of chemistry in recent decades, such NGs and GNRs with unique zigzag peripheries are now synthetically accessible. This chapter discusses several strategies for the synthesis of zigzag-edged NGs and GNRs, their structural characterization, physical properties, and potential applications.

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Novoselov KS, Geim AK, Morozov SV, Jiang D, Zhang Y, Dubonos SV, Grigorieva IV, Firsov AA (2004) Science 306:666–669CrossRef

Novoselov KS, Geim AK, Morozov SV, Jiang D, Katsnelson MI, Grigorieva IV, Dubonos SV, Firsov AA (2005) Nature 438:197–200CrossRef

Novoselov KS, Fal’ko VI, Colombo L, Gellert PR, Schwab MG, Kim K (2012) Nature 490:192–200CrossRef

Castro-Neto AH, Guinea F, Peres NMR, Novoselov KS, Geim AK (2009) Rev Mod Phys 81:109–162CrossRef

Gemayel ME, Narita A, Dössel LF, Sundaram RS, Kiersnowski A, Pisula W, Hansen MR, Ferrari AC, Orgiu E, Feng X, Müllen K, Samori P (2014) Nanoscale 6:6301–6314CrossRef

Wang X, Ouyang Y, Li X, Wang H, Guo J, Dai H (2008) Phys Rew Lett 100:206803CrossRef

Ritter KA, Lyding JW (2009) Nat Mater 8:235–242CrossRef

Han M, Özyilmaz B, Zhang Y, Kim P (2007) Phys Rev Lett 98:206805CrossRef

Yazyev O (2013) Acc Chem Res 46:2319–2328CrossRef

10.

Datta SS, Strachan DR, Khamis SM, Johnson ATC (2008) Nano Lett 8:1912–1915CrossRef

11.

Campos-Delgado J, Romo-Herrera J, Jia X, Cullen D, Muramatsu H, Kim Y, Hayashi T, Ren Z, Smith D, Okuno Y, Ohba T, Kanoh H, Kaneko K, Endo M, Terrones H, Dresselhaus M, Terrones M (2008) Nano Lett 8:2773–2778CrossRef

12.

Chen ZH, Lin YM, Rooks MJ, Avouris P (2007) Phys E 40:228–232CrossRef

13.

Elías A, Botello-Méndez A, Meneses-Rodríguez D, González V, Ramírez-González D, Ci L, Muñoz-Sandoval E, Ajayan M, Terrones H, Terrones M (2010) Nano Lett 10:366–372CrossRef

14.

Jiao L, Wang X, Diankov G, Wang H, Dai H (2010) Nat Nano 5:321–325CrossRef

15.

Pan Z, Liu N, Fu L, Liu Z (2011) J Am Chem Soc 133:17578–17581CrossRef

16.

Sakaguchi H, Kawagoe Y, Hirano Y, Iruka T, Yano M, Nakae T (2014) Adv Mater 26:4134–4138CrossRef

17.

Wu J, Gherghel L, Watson M, Li J, Wang Z, Simpson C, Kolb U, Müllen K (2003) Macromolecules 36:7082–7089CrossRef

18.

Yang X, Dou X, Rouhanipour A, Zhi L, Räder H, Müllen K (2008) J Am Chem Soc 130:4216–4217CrossRef

19.

Fogel Y, Zhi L, Rouhanipour A, Andrienko D, Räder H, Müllen K (2009) Macromolecule 42:6878–6884CrossRef

20.

Schwab MG, Narita N, Hernandez Y, Balandina Y, Mali KS, Feyter SD, Feng X, Müllen K (2012) J Am Chem Soc 134:18169–18172CrossRef

21.

Dössel L, Gherghel L, Feng X, Müllen K (2011) Angew Chem Int Ed 50:2540–2543CrossRef

22.

Son YW, Cohen ML, Louie SG (2006) Nature 444:347–349CrossRef

23.

Wu J, Pisula W, Müllen K (2007) Chem Rev 107:718–747CrossRef

24.

Chen L, Hernandez Y, Feng X, Müllen K (2012) Angew Chem Int Ed 51:7640–7654CrossRef

25.

Clar E (1972) The aromatic sextet. London, Wiley

26.

Feng X, Pisula W, Müllen K (2009) Pure Appl Chem 81:2203–2224CrossRef

27.

Stabel A, Herwig P, Müllen K, Rabe JP (1995) Angew Chem Int Ed 34:1609–1611CrossRef

28.

Rieger R, Müllen K (2010) J Phys Org Chem 23:315–325

29.

Pisula W, Feng X, Müllen K (2011) Chem Mater 23:554–567CrossRef

30.

Liu J, Li BW, Tan YZ, Giannakopoulos A, Sanchez-Sanchez C, Ruffieux P, Beljonne D, Fasel R, Feng X, Müllen K (2015) J Am Chem Soc 137:6097–6103CrossRef

31.

Reid DH (1958) Tetrahedron 3:339–352CrossRef

32.

Morita Y, Suzuki S, Sato K, Takui T (2011) Nat Chem 3:197–204CrossRef

33.

Purushothaman B, Bruzek M, Parkin SR, Miller AF, Anthony JE (2011) Angew Chem Int Ed 50:7013–7017CrossRef

34.

Stein SE, Brown RL (1987) J Am Chem Soc 109:3721–3729CrossRef

35.

Wang Z, Tomović Ź, Kastler M, Pretsch R, Negri F, Enkelmann V, Müllen K (2004) J Am Chem Soc 126:7794–7795CrossRef

36.

Kastler M, Schmidt J, Pisula W, Sebastiani D, Müllen K (2006) J Am Chem Soc 128:9526–9534CrossRef

37.

Lowe JP (1982) Int J Quantum Chem Quantum Biol Symp 9:5–13

38.

Dumslaff T, Yang B, Maghsoumi A, Velpula G, Mali KS, Castiglioni C, Feyter SD, Tommasini M, Narita A, Feng X, Müllen K (2016) J Am Chem Soc 138:4726–4729CrossRef

39.

Alibert-Fouet S, Seguy I, Bobo JF, Destruel P, Bock H (2007) Chem Eur J 13:1746–1753CrossRef

40.

Rädulescu D, Ostrogovich G, Bärbulescu F (1931) Chem Ber 64:2240–2242CrossRef

41.

Kono Y, Miyamoto H, Aso Y, Otsubo T, Ogura F, Tanaka T, Sawada M (1989) Angew Chem Int Ed 28:1222–1223CrossRef

42.

Schoental R, Scott EJY (1949) J Chem Soc:1683–1696

43.

Berlman IB (1973) Energy transfer parameters of aromatic compounds. Academic, London

44.

Mi BX, Gao ZQ, Lee CS, Lee ST, Kwong HL, Wong NB (1999) Appl Phys Lett 75:4055–4057CrossRef

45.

Clar E (1948) Chem Ber 81:62

46.

Arabei SM, Pavich TA (2000) J Appl Spectrosc 67:236–244CrossRef

47.

Hirao Y, Konishi A, Matsumoto K, Kurata H, Kubo T (2012) AIP Conf Proc 1504:863–866CrossRef

48.

Li J, Zhang K, Zhang X, Huang KW, Chi C, Wu J (2010) J Org Chem 75:856–863CrossRef

49.

Konishi A, Hirao Y, Nakano M, Shimizu A, Botek E, Champagne B, Shiomi D, Sato K, Takui T, Matsumoto K, Kurata H, Kubo T (2010) J Am Chem Soc 132:11021–11023CrossRef

50.

Konishi A, Hirao Y, Matsumoto K, Kurata H, Kishi R, Shigeta Y, Nakano M, Tokunaga K, Kamada K, Kubo T (2013) J Am Chem Soc 135:1430–1437CrossRef

51.

Konishi A, Hirao Y, Kurata H, Kubo T, Nakano M, Kamada K (2014) Pure Appl. Chem 86:497–505

52.

Konishi A, Hirao Y, Kurata H, Kubo T (2013) Solid State Commun 175-176:62–70CrossRef

53.

Motta SD, Negri F, Fazzi D, Castiglioni C, Canesi EV (2010) J Phys Chem Lett 1:3334–3339CrossRef

54.

Sun Z, Wu J (2012) J Mater Chem 22:4151–4160CrossRef

55.

Sun Z, Ye Q, Chi C, Wu J (2012) Chem Soc Rev 41:7857–7889CrossRef

56.

Fort EH, Donovan PM, Scott LT (2009) J Am Chem Soc 131:16006–16007CrossRef

57.

Jiang DE, Dai S (2008) Chem Phys Lett 466:72–75CrossRef

58.

Moscardó F, San-Fabián E (2009) Chem Phys Lett 480:26–30CrossRef

59.

Liu J, Ravat P, Wagner M, Baumgarten M, Feng X, Müllen K (2015) Angew Chem Int Ed 54:12442–12446CrossRef

60.

Chase DT, Fix AG, Rose BD, Weber CD, Nobusue S, Stockwell CE, Zakharov LN, Lonergan MC, Haley MM (2011) Angew Chem Int Ed 50:11103–11106CrossRef

61.

Chase DT, Rose BD, McClintock SP, Zakharov LN, Haley MM (2011) Angew Chem Int Ed 50:1127–1130CrossRef

62.

Liu J, Narita A, Osella S, Zhang W, Schollmeyer D, Beljonne D, Feng X, Müllen K (2016) J Am Chem Soc 138:2602–2608CrossRef

63.

Gu X, Xu X, Li H, Liu Z, Miao Q (2015) J Am Chem Soc 137:16203–16208CrossRef

64.

Liu J, Osella S, Ma J, Berger R, Schollmeyer D, Beljonne D, Feng X, Müllen K (2016) J Am Chem Soc 138:8364–8367CrossRef

65.

Zhang X, Li J, Qu H, Chi C, Wu J (2010) Org Lett 12:3946–3949CrossRef

66.

Zöphel L, Berger R, Gao P, Enkelmann V, Baumgarten M, Wagner M, Müllen K (2013) Chem Eur J 19:17821–17826CrossRef

67.

Rogers C, Chen C, Pedramrazi Z, Omrani AA, Tsai HZ, Jung HS, Lin S, Crommie MF, Fischer FR (2015) Angew Chem Int Ed 54:15143–15146CrossRef

68.

Reid DH (1956) Chem Ind:1504

69.

Sogo PB, Nakazaki M, Calvin M (1957) J Chem Phys 26:1343–1345CrossRef

70.

Reid DH, Fraser M, Molloy BB, Payne HAS, Sutherland RG (1961) Tetrahedron Lett 15:530–535CrossRef

71.

Goto K, Kubo T, Yamamoto K, Nakasuji K, Sato K, Shiomi D, Takui T, Kubota M, Kobayashi T, Yakusi K, Ouyang JY (1999) J Am Chem Soc 121:1619–1620CrossRef

72.

Zaitsev V, Rosokha SV, Head-Gordon M, Kochi JK (2006) J Org Chem 71:520–526CrossRef

73.

Nakasuji K, Yoshida K, Murata I (1983) J Am Chem Soc 105:5136–5137CrossRef

74.

Murata I, Sasaki S, Klabunde KU, Toyoda J, Nakasuji K (1991) Angew Chem Int Ed 30:172–173CrossRef

75.

Ohashi K, Kubo T, Masui T, Yamamoto K, Nakasuji K, Takui T, Kai Y, Murata I (1998) J Am Chem Soc 120:2018–2027CrossRef

76.

Kubo T, Shimizu A, Sakamoto M, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Morita Y, Nakasuji K (2005) Angew Chem Int Ed 44:6564–6568CrossRef

77.

Shimizu A, Uruichi M, Yakushi K, Matsuzaki H, Okamoto H, Nakano M, Hirao Y, Matsumoto K, Kurata H, Kubo T (2009) Angew Chem Int Ed 48:5482–5486CrossRef

78.

Kubo T, Shimizu A, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Morita Y, Nakasuji K (2007) Org Lett 9:81–84CrossRef

79.

Shimizu A, Hirao Y, Matsumoto K, Kurata H, Kubo T, Uruichi M, Yakushi K (2012) Chem Commun 48:5629–5631CrossRef

80.

Shimizu A, Kubo T, Uruichi M, Yakushi K, Nakano M, Shiomi D, Sato K, Takui T, Hirao Y, Matsumoto K, Kurata H, Morita Y, Nakasuji K (2010) J Am Chem Soc 132:14421–14428CrossRef

81.

Kubo T (2015) Chem Rec 15:218–232CrossRef

82.

Kubo T (2015) Chem Lett 44:111–122CrossRef

83.

Clar E, Lang KF, Schulz-Kiesow H (1955) Chem Ber 88:1520–1527CrossRef

84.

Staab HA, Nissen A, Ipaktschi J (1968) Angew Chem Int Ed 7:226–226CrossRef

85.

Mitchell RH, Sondheimer F (1970) Tetrahedron 26:2141–2150CrossRef

86.

Staab HA, Ipaktschi J, Nissen A (1971) Chem Ber 104:1182–1186CrossRef

87.

Umeda R, Hibi D, Miki K, Tobe Y (2009) Org Lett 11:4104–4106CrossRef

88.

Umeda R, Hibi D, Miki K, Tobe Y (2010) Pure Appl Chem 82:871–878CrossRef

89.

Wu TC, Chen CH, Hibi D, Shimizu A, Tobe Y, Wu YT (2010) Angew Chem Int Ed 49:7059–7062CrossRef

90.

Shan L, Liang Z, Xu X, Tang Q, Miao Q (2013) Chem Sci 4:3294–3297CrossRef

91.

Sun Z, Zeng Z, Wu J (2013) Chem Asian J 8:2894–2904CrossRef

92.

Sun Z, Zeng Z, Wu J (2014) Acc Chem Res 47:2582–2591CrossRef

93.

Li Y, Heng WK, Lee BS, Aratani N, Zafra JL, Bao N, Lee R, Sung YM, Sun Z, Huang KW, Webster RD, López Navarrete JT, Kim DH, Osuka A, Casado J, Ding J, Wu J (2012) J Am Chem Soc 134:14913–14922CrossRef

94.

Nakano M, Kishi R, Takebe A, Nate M, Takahashi H, Kubo T, Kamada K, Ohta K, Champagne B, Botek E (2007) Comput Lett 3:333–338CrossRef

95.

Weil T, Vosch T, Hofkens J, Peneva K, Müllen K (2010) Angew Chem Int Ed 49:9068–9093CrossRef

96.

Anthony J (2008) Angew Chem Int Ed 47:452–483CrossRef

97.

Zeng W, Sun Z, Herng TS, Gonçalves TP, Gopalakrishna TY, Huang KW, Ding J, Wu J (2016) Angew Chem Int Ed 55:8615–8619CrossRef

98.

Stępień M, Gońka E, Żyła M (2016) N. Sprutta Chem Rev 117:3479–3716CrossRef

99.

Liu Z, Marder TB (2008) Angew Chem Int Ed 47:242–244CrossRef

100.

Bosdet MJD, Piers WE (2009) Can J Chem 87:8–29CrossRef

101.

Campbell PG, Marwitz AJV, Liu SY (2012) Angew Chem Int Ed 51:6074–6092CrossRef

102.

Wang XY, Wang JY, Pei J (2015) Chem Eur J 21:3528–3539CrossRef

103.

Aramaki Y, Omiya H, Yamashita M, Nakabayashi K, Ohkoshi SI, Nozaki K (2012) J Am Chem Soc 134:19989–19992CrossRef

104.

Suzuki S, Yoshida K, Kozaki M, Okada K (2013) Angew Chem Int Ed 52:2499–2502CrossRef

105.

Rosenthal AJ, Devillard M, Miqueu K, Bouhadir G, Bourissou D (2015) Angew Chem Int Ed 54:9198–9202CrossRef

106.

Katayama T, Nakatsuka S, Hirai H, Yasuda N, Kumar J, Kawai T, Hatakeyama T (2016) J Am Chem Soc 138:5210–5213CrossRef

107.

Wang XY, Narita A, Zhang W, Feng X, Müllen K (2016) J Am Chem Soc 138:9021–9024CrossRef

108.

Wang X, Zhang F, Schellhammer KS, Machata P, Ortmann F, Cuniberti G, Fu Y, Hunger J, Tang R, Popov AA, Berger R, Müllen K, Feng X (2016) J Am Chem Soc 138:11606–11615CrossRef

109.

Ajayakumar M, Asthana D, Mukhopadhyay P (2012) Org Lett 14:4822–4825CrossRef

110.

Wu X, Guo Z, Wu Y, Zhu S, James TD, Zhu W (2013) ACS Appl Mater Interfaces 5:12215–12220CrossRef

111.

Jung JY, Kang M, Chun J, Lee J, Kim J, Kim J, Kim Y, Kim SJ, Lee C, Yoon J (2013) Chem Commun 49:176–178CrossRef

112.

Ji L, Edkins RM, Lorbach A, Krummenacher I, Brückner C, Eichhorn A, Braunschweig H, Engels B, Low PJ, Marder TB (2015) J Am Chem Soc 137:6750–6753CrossRef

113.

Narita A, Feng X, Hernandez Y, Jensen SA, Bonn M, Yang H, Verzhbitskiy IA, Casiraghi C, Hansen MR, Koch AHR, Fytas G, Ivasenko O, Li B, Mali KS, Tatyana B, Mahesh S, Feyter SD, Müllen K (2014) Nat Chem 6:126–132CrossRef

114.

Cai J, Pignedoli CA, Talirz L, Ruffieux P, Söde H, Liang L, Meunier V, Berger R, Li R, Feng X, Müllen K, Fasel R (2014) Nat Nano 9:896–900CrossRef

115.

Narita A, Verzhbitskiy IA, Frederickx W, Mali KS, Jensen SN, Hansen MR, Bonn M, Feyter SD, Casiragh C, Feng X, Müllen K (2014) ACS Nano 8:11622–11630CrossRef

116.

Cai J, Ruffieux P, Jaafar R, Bieri M, Braun T, Blankenburg S, Muoth M, Seitsonen P, Saleh M, Feng X, Müllen K, Fasel R (2010) Nature 466:470–473CrossRef

117.

Nakada K, Fujita M, Dresselhaus G, Dresselhaus MS (1996) Phys Rev B 54:17954–17961CrossRef

118.

Son YW, Cohen ML, Louie SG (2007) Phys Rev Lett 98:216803CrossRef

119.

Talirz L, Sode H, Cai J, Ruffieux P, Blankenburg S, Jafaar R, Berger R, Feng X, Müllen K, Passerone D, Fasel R, Pignedoli CA (2013) J Am Chem Soc 135:2060–2063CrossRef

120.

Ijas M, Ervasti M, Uppstu A, Liljeroth P, van der Lit J, Swart I, Harju A (2013) Phys Rev B 88:075429CrossRef

121.

Magda GZ, Jin XZ, Hagymasi I, Vancso P, Osvath Z, Nemes-Incze P, Hwang CY, Biro LP, Tapaszto L (2014) Nature 514:608–611CrossRef

122.

Ruffieux P, Wang S, Yang B, Sánchez-Sánchez C, Liu J, Dienel T, Talirz L, Shinde P, Pignedoli CA, Passerone D, Dumslaff T, Feng X, Müllen K, Fasel R (2016) Nature 531:489–492CrossRef

123.

Gross L, Mohn F, Moll N, Liljeroth P, Meyer G (2009) Science 325:1110–1114CrossRef

124.

Li Y, Zhang W, Morgenstern M, Mazzarello R (2013) Phys Rev Lett 110:216804CrossRef

125.

Repp J, Meyer G, Paavilainen S, Olsson FE, Persson M (2005) Phys Rev Lett 95:225503CrossRef

126.

Hybertsen MS, Louie SG (1986) Phys Rev B 34:5390CrossRef

127.

Tao C, Jiao L, Yazyev OV, Chen YC, Feng J, Zhang X, Capaz RB, Tour JM, Zettl A, Louie SG, Dai H, Crommie MF (2011) Nat Phys 7:616–620CrossRef

128.

van der Lit J, Boneschanscher MP, Vanmaekelbergh D, Ijas M, Uppstu A, Ervasti M, Harju A, Liljeroth P, Swart I (2013) Nat Commun 4:2023

Title: Nanographenes and Graphene Nanoribbons with Zigzag-Edged Structures
Authors: Junzhi Liu
Reinhard Berger
Klaus Müllen
Xinliang Feng
Publisher: Springer International Publishing
Book: From Polyphenylenes to Nanographenes and Graphene Nanoribbons
Print ISBN: 978-3-319-64169-0

Electronic ISBN: 978-3-319-64170-6

Copyright Year: 2017
DOI: https://doi.org/10.1007/12_2017_1

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