Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Junzhi Liu; Xinliang Feng

doi:10.1055/s-0039-1690767

Synlett, Table of Contents

Synlett 2020; 31(03): 211-222
DOI: 10.1055/s-0039-1690767

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Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Junzhi Liu ∗

^aDepartment of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China Email: juliu@hku.hk

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany Email: xinliang.feng@tu-dresden.de

,

Xinliang Feng ∗

^bCenter for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany Email: xinliang.feng@tu-dresden.de

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Abstract

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Abstract

Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary account of the preparation of nitrogen-doped PAHs (N-PAHs) through 1,3-dipolar cycloaddition between different dipolarophiles, as well as pyrazine-type N-doped diaza-hexa-peri-hexabenzocoronene (diaza-HBC). Additionally, we present the synthesis of a class of helical N-charged PAHs, including one charged aza[5]helicene and two charged aza[4]helicenes. Moreover, the bottom-up organic synthesis strategy is further extended to the construction of novel nitrogen-boron-nitrogen (NBN)-containing PAHs. Finally, we discuss the synthesis of four-coordinate boron chromophores containing 6,12,18-tris(alkyl amine)-5,11,17-triazatrinaphthylene derivative ligands.

1 Introduction

2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP)

3 Cationic Nitrogen-Doped Helical PAHs

4 Nitrogen–Boron–Nitrogen-Doped PAHs

5 Conclusion and Outlook

Key words

polycyclic aromatic hydrocarbons - nanographenes - heteroatoms - nitrogen doping - boron doping

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References

References
1 Wu J, Pisula W, Müllen K. Chem. Rev. 2007; 107: 718
2 Chen L, Hernandez Y, Feng X, Müllen K. Angew. Chem. Int. Ed. 2012; 51: 7640
3 Clar E. Polycyclic Hydrocarbons. Academic Press; London/New York: 1964
4 Clar E. The Aromatic Sextet. Wiley; London: 1972
5 Pisula W, Feng X, Müllen K. Chem. Mater. 2011; 23: 554
6 Avlasevich Y, Li C, Müllen K. J. Mater. Chem. 2010; 20: 3814
7 Feng X, Pisula W, Müllen K. Pure Appl. Chem. 2009; 81: 2203
8 Narita A, Wang X.-Y, Feng X, Müllen K. Chem. Soc. Rev. 2015; 44: 6616
9 Wang X.-Y, Narita A, Müllen K. Nat. Rev. Chem. 2017; 2: 00100
10 Stabel A, Herwig P, Müllen K, Rabe JP. Angew. Chem., Int. Ed. Engl. 1995; 34: 1609
11 Schmidt-Mende L, Fechtenkötter A, Müllen K, Moons E, Friend RH, MacKenzie JD. Science 2001; 293: 1119
12 Hill JP, Jin WS, Kosaka A, Fukushima T, Ichihara H, Shimomura T, Ito K, Hashizume T, Ishii N, Aida T. Science 2004; 304: 1481
13 Jäckel F, Watson MD, Müllen K, Rabe JP. Phys. Rev. Lett. 2004; 92: 188303
14 Hendel W, Khan ZH, Schmidt W. Tetrahedron 1986; 42: 1127
15 Wang ZH, Tomovic Z, Kastler M, Pretsch R, Negri F, Enkelmann V, Müllen K. J. Am. Chem. Soc. 2004; 126: 7794
16 Konishi A, Hirao Y, Kurata H, Kubo T. Solid State Commun. 2013; 62
17 Kubo T. Chem. Lett. 2015; 44: 111
18 Kubo T. Chem. Rec. 2015; 15: 18
19 Konishi A, Kubo T. Top Curr. Chem. 2017; 375: 83
20 Sun Z, Zeng Z, Wu J. Acc. Chem. Res. 2014; 47: 2582
21 Zeng Z, Shi X, Chi C, Navarrete JT. L, Casado J, Wu J. Chem. Soc. Rev. 2015; 44: 6578
22 Schwarze M, Tress W, Beyer B, Gao F, Scholz R, Poelking C, Ortstein K, Günther AA, Kasemann D, Andrienko D, Leo K. Science 2016; 352: 1446
23 Wang X, Sun G, Routh P, Kim D.-H, Huang W, Chen P. Chem. Soc. Rev. 2014; 43: 7067
24 Maiti UN, Lee WJ, Lee JM, Oh Y, Kim JY, Kim JE, Shim J, Han TH, Kim SO. Adv. Mater. 2014; 26: 40
25 Liu HT, Liu Y, Zhu D. J. Mater. Chem. 2011; 21: 3335
26 Bunz UH. F, Engelhart JU, Lindner BD, Schaffroth M. Angew. Chem. Int. Ed. 2013; 52: 3810
27 Mateo-Alonso A. Chem. Soc. Rev. 2014; 43: 6311
28 Scholl R. Ber. Dtsch. Chem. Ges. 1907; 40: 1691
29 Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
30 Ambrosi A, Chua CK, Bonanni A, Pumera M. Chem. Rev. 2014; 114: 7150
31 Wang X.-Y, Wang J.-Y, Pei J. Chem. Eur. J. 2015; 21: 3528
32 Katritzky AR. Advances in Heterocyclic Chemistry, Vol. 55. Academic Press; New York: 1992: 261-358
33 Wu D, Zhi L, Bodwell GJ, Cui G, Tsao N, Müllen K. Angew. Chem. Int. Ed. 2007; 46: 5417
34 Wu D, Pisula W, Enkelmann V, Feng X, Müllen K. J. Am. Chem. Soc. 2009; 131: 9620
35 Dral PO, Kivala M, Clark T. J. Org. Chem. 2013; 78: 1894
36 Tan Q, Higashibayashi S, Karanjit S, Sakurai H. Nat. Commun. 2012; 3: 891
37 Draper SM, Gregg DJ, Madathil R. J. Am. Chem. Soc. 2002; 124: 3486
38 Ito S, Tokimaru Y, Nozaki K. Angew. Chem. Int. Ed. 2015; 54: 7256
39 Yokoi H, Hiraoka Y, Hiroto S, Sakamaki D, Seki S, Shinokubo H. Nat. Commun. 2015; 6: 8215
40 Park YS, Dibble DJ, Kim J, Lopez RC, Vargas E, Gorodetsky AA. Angew. Chem. Int. Ed. 2016; 55: 3352
41 Bunz UH. F. Acc. Chem. Res. 2015; 48: 1676
42 Ishi-i T, Yaguma K, Kuwahara R, Taguri Y, Mataka S. Org. Lett. 2006; 8: 585
43 Roussel O, Kestemont G, Tant J, Halleux VD, Aspe RG, Levin J, Remacle A, Gearba IR, Ivanov D, Lehmann M, Geerts Y. Mol. Cryst. Liq. Cryst. 2003; 396: 35
44 Sergeyev S, Pisula W, Geerts YH. Chem. Soc. Rev. 2007; 36: 1902
45 Lee WJ, Maiti UN, Lee JM, Lim J, Han TH, Kim SO. Chem. Commun. 2014; 50: 6818
46 Kim J, Lee K, Woo SI, Jung Y. Phys. Chem. Chem. Phys. 2011; 13: 17505
47 Parvez K, Yang S, Hernandez Y, Winter A, Turchanin A, Feng X, Müllen K. ACS Nano 2012; 6: 9541
48 Liang H, Zhuang X, Brüller S, Feng X, Müllen K. Nat. Commun. 2014; 5: 4973
49 Deng Y, Xie Y, Zou K, Ji X. J. Mater. Chem. A 2016; 4: 1144
50 Huisgen R. Angew. Chem., Int. Ed. Engl. 1963; 2: 565
51 Harwood LM, Vickers RJ. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products. John Wiley & Sons; New York: 2003: 169-252
52 Domingo LR, Chamorro E, Perez P. Lett. Org. Chem. 2010; 7: 432
53 Kahn SD, Hehre WJ, Pople JA. J. Am. Chem. Soc. 1987; 109: 1871
54 Beugelmans R, Benadjila-Iguertsira L, Roussi G. J. Chem. Soc., Chem. Commun. 1982; 544
55 Padwa A, Dent W, Nimmesgern H, Venkatramanan MK, Wong GS. K. Chem. Ber. 1986; 119: 813
56 Braida B, Walter C, Engels B, Hiberty PC. J. Am. Chem. Soc. 2010; 132: 7631
57 Ess DH, Houk KN. J. Am. Chem. Soc. 2008; 130: 10187
58 Lopez-Calle E, Keller M, Eberbach W. Eur. J. Org. Chem. 2003; 1438
59 Terao Y, Aono M, Achiwa K. Heterocycles 1988; 27: 981
60 Grigg R, Malone JF, Mongkolaussavaratana T, Thianpatanagul S. J. Chem. Soc., Chem. Commun. 1986; 421
61 D’Amico JJ, Stults BR, Ruminski PG, Wood KV. J. Heterocycl. Chem. 1983; 20: 1283
62 Romming C, Kolsaker P. Acta Chem. Scand., Ser. B 1978; 32: 679
63 Takahashi S, Kano H. J. Org. Chem. 1965; 30: 1118
64 Najera C, Sansano JM. Curr. Org. Chem. 2003; 7: 1105
65 Berger R, Giannakopoulos A, Ravat P, Wagner M, Beljonne D, Feng X, Müllen K. Angew. Chem. Int. Ed. 2014; 53: 10520
66 Berger R, Wagner M, Feng X, Müllen K. Chem. Sci. 2015; 6: 436
67 Chintawar CC, Mane MV, Tathe AG, Biswas S, Patil NT. Org. Lett. 2019; 21: 7109
68 Wang X.-Y, Richter M, He Y, Björk J, Riss A, Rajesh R, Garnica M, Hennersdorf F, Weigand JJ, Narita A, Berger R, Feng X, Auwärter W, Barth JV, Palma C.-A, Müllen K. Nat. Commun. 2017; 8: 1948
69 Li Y, Huang K.-W, Sun Z, Webster RD, Zeng Z, Zeng W, Chi C, Furukawa K, Wu J. Chem. Sci. 2014; 5: 1908
70 Li Y, Heng W.-K, Lee BS, Aratani N, Zafra JL, Bao N, Lee R, Sung YM, Sun Z, Huang K.-W, Webster RD, Navarrete JT. L, Kim D, Osuka A, Casado J, Ding J, Wu J. J. Am. Chem. Soc. 2012; 134: 14913
71 Clar E, Fell GS, Richmond MH. Tetrahedron 1960; 9: 96
72 Ito S, Tokimaru Y, Nozaki K. Chem. Commun. 2015; 51: 221
73 Ito S, Tokimaru Y, Nozaki K. Angew. Chem. Int. Ed. 2015; 54: 7256
74 Tokimaru Y, Ito S, Nozaki K. Angew. Chem. Int. Ed. 2017; 56: 15560
75 Tokimaru Y, Ito S, Nozaki K. Angew. Chem. Int. Ed. 2018; 57: 9818
76 Lee WJ, Maiti UN, Lee JM, Lim J, Han TH, Kim SO. Chem. Commun. 2014; 50: 6818
77 Kim J, Lee K, Woo SI, Jung Y. Phys. Chem. Chem. Phys. 2011; 13: 17505
78 Sucunzam D, Cuadro AM, Alvarez-Builla J, Vaquero JJ. J. Org. Chem. 2016; 81: 10126
79 Li F, Cho J, Tan S, Kim S. Org. Lett. 2018; 20: 824
80 Mule RD, Shaikh AC, Gadeab AB, Patil NT. Chem. Commun. 2018; 54: 11909
81 Toriumi N, Asano N, Miyamoto K, Muranaka A, Uchiyama M. J. Am. Chem. Soc. 2018; 140: 3858
82 Yang Y, Liu D, Song M, Shi D, Liu B, Cheng K, Lu Y, Liu H, Yang M, Wang W, Li J, Wei J. Chem. Eur. J. 2017; 23: 7409
83 Asanuma Y, Eguchi H, Nishiyama H, Tomita I, Inagi S. Org. Lett. 2017; 19: 1824
84 Villar JM, Suárez J, Varela JA, Saá C. Org. Lett. 2017; 19: 1702
85 Xiao S, Myers M, Miao Q, Sanaur S, Pang K, Steigerwald ML, Nuckolls C. Angew. Chem. Int. Ed. 2005; 44: 7390
86 Xiao S, Kang SJ, Wu Y, Ahn S, Kim JB, Loo Y, Siegrist T, Steigerwald ML, Li H, Nuckolls C. Chem. Sci. 2013; 4: 2018
87 Liu J, Li B, Tan Y, Giannakopoulos A, Sanchez-Sanchez C, Beljonne D, Ruffieux P, Fasel R, Feng X, Müllen K. J. Am. Chem. Soc. 2015; 137: 6097
88 Ma J, Liu J, Baumgarten M, Fu Y, Tan Y, Schellhammer KS, Ortmann F, Cuniberti G, Komber H, Berger R, Müllen K, Feng X. Angew. Chem. Int. Ed. 2017; 56: 3280
89 Ball M, Zhong Y, Wu Y, Schenck C, Ng F, Steigerwald M, Xiao S, Nuckolls C. Acc. Chem. Res. 2015; 48: 267
90 Shen Y, Chen C. Chem. Rev. 2012; 112: 1463
91 Gingras M. Chem. Soc. Rev. 2013; 42: 968
92 Gingras M, Félix G, Peresutti R. Chem. Soc. Rev. 2013; 42: 1007
93 Gingras M. Chem. Soc. Rev. 2013; 42: 1051
94 Kiran V, Mathew SP, Cohen SP, Delgado IH, Lacour J, Naaman R. Adv. Mater. 2016; 28: 1957
95 Naaman R, Waldeck DH. Annu. Rev. Phys. Chem. 2015; 66: 263
96 Deng J.-R, Chan W.-C, Lai NC.-H, Yang B, Tsang C.-S, Ko BC.-B, Chan SL.-F, Wong M.-K. Chem. Sci. 2017; 8: 7537
97 Xu K, Fu Y, Zhou Y, Hennersdorf F, Machata P, Vincon I, Weigand JJ, Popov AA, Berger R, Feng X. Angew. Chem. Int. Ed. 2017; 56: 15876
98 Zhang G, Yang L, Wang Y, Xie Y, Huang H. J. Am. Chem. Soc. 2013; 135: 8850
99 Davies DL, Ellul CE, Macgregor SA, McMullin CL, Singh K. J. Am. Chem. Soc. 2015; 137: 30, 9659
100 Fukazawa A, Yamada H, Yamaguchi S. Angew. Chem. Int. Ed. 2008; 47: 5582
101 Payne MM, Odom SA, Parkin SR, Anthony JE. Org. Lett. 2004; 6: 3325
102 Niimi K, Shinamura S, Osaka I, Miyazaki E, Takimiya K. J. Am. Chem. Soc. 2011; 133: 8732
103 Mori T, Nishimura T, Yamamoto T, Doi I, Miyazaki E, Osaka I, Takimiya K. J. Am. Chem. Soc. 2013; 135: 13900
104 Bosdet MJ. D, Jaska CA, Piers WE, Sorensen TS, Parvez M. Org. Lett. 2007; 9: 1395
105 Liu Z, Marder TB. Angew. Chem. Int. Ed. 2008; 47: 242
106 Bosdet MJ. D, Piers WE. Can. J. Chem. 2009; 87: 8
107 Campbell PG, Marwitz AJ. V, Liu S.-Y. Angew. Chem. Int. Ed. 2012; 51: 6074
108 Hashimoto S, Ikuta T, Shiren K, Nakatsuka S, Ni J, Nakamura M, Hatakeyama T. Chem. Mater. 2014; 26: 6265
109 Wang X.-Y, Lin HR, Lei T, Yang DC, Zhuang FD, Wang JY, Yuan SC, Pei J. Angew. Chem. Int. Ed. 2013; 52: 3117
110 Wang X.-Y, Zhuang FD, Wang RB, Wang XC, Cao XY, Wang JY, Pei J. J. Am. Chem. Soc. 2014; 136: 3764
111 Wang X.-Y, Wang JY, Pei J. Chem. Eur. J. 2015; 21: 3528
112 Wang X.-Y, Narita A, Feng X, Müllen K. J. Am. Chem. Soc. 2015; 137: 7668
113 Wang X, Zhang F, Liu J, Tang R, Fu Y, Wu D, Xu Q, Zhuang X, He G, Feng X. Org. Lett. 2013; 15: 5714
114 Zhang W, Zhang F, Tang R, Fu Y, Wang X, Zhuang X, He G, Feng X. Org. Lett. 2016; 18: 3618
115 Chissick SS, Dewar MJ. S, Maitlis PM. Tetrahedron Lett. 1960; 1: 8
116 Hatakeyama T, Hashimoto S, Seki S, Nakamura M. J. Am. Chem. Soc. 2011; 133: 18614
117 Wang X, Zhang F, Gao J, Fu Y, Zhao W, Tang R, Zhang W, Zhuang X, Feng X. J. Org. Chem. 2015; 80: 10127
118 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. J. Am. Chem. Soc. 2016; 138: 11606
119 Riehm T, Paoli GD, Wadepohl H, Cola LD, Gade LH. Chem. Commun. 2008; 42: 5348
120 Nishida J.-I, Fujita T, Fujisaki Y, Tokito S, Yamashita Y. J. Mater. Chem. 2011; 21: 16442
121 Abbey ER, Liu S.-Y. Org. Biomol. Chem. 2013; 11: 2060
122 Lorenz T, Lik A, Plamper FA, Helten H. Angew. Chem. Int. Ed. 2016; 55: 7236
123 Numano M, Nagami N, Nakatsuka S, Katayama T, Nakajima K, Tatsumi S, Yasuda N, Hatakeyama T. Chem. Eur. J. 2016; 22: 11574
124 Noda H, Furutachi M, Asada Y, Shibasaki M, Kumagai N. Nat. Chem. 2017; 9: 571
125 Fingerle M, Maichle-Mössmer C, Schundelmeier S, Speiser B, Bettinger HF. Org. Lett. 2017; 19: 4428
126 Fu Y, Zhang K, Dmitrieva E, Liu F, Ma J, Weigand JJ, Popov AA, Berger R, Pisula W, Liu J, Feng X. Org. Lett. 2019; 21: 1354
127 Li D, Zhang H, Wang Y. Chem. Soc. Rev. 2013; 42: 8416
128 Galer P, Korošec RC, Vidmar M, Šket B. J. Am. Chem. Soc. 2014; 136: 7383
129 Fu Y, Qiu F, Zhang F, Mai Y, Wang Y, Fu S, Tang R, Zhuang X, Feng X. Chem. Commun. 2015; 51: 5298
130 Sun L, Zhang F, Wang X, Qiu F, Xue M, Tregnago G, Cacialli F, Osella S, Beljonne D, Feng X. Chem. Asian J. 2015; 10: 709
131 Cheng X, Li D, Zhang Z, Zhang H, Wang Y. Org. Lett. 2014; 16: 880
132 Wakamiya A, Taniguchi T, Yamaguchi S. Angew. Chem. Int. Ed. 2006; 45: 3170
133 Liu QD, Mudadu MS, Thummel R, Tao Y, Wang S. Adv. Funct. Mater. 2005; 15: 143
134 Tamgho I.-S, Hasheminasab A, Engle JT, Nemykin VN, Ziegler CJ. J. Am. Chem. Soc. 2014; 136: 5623
135 Zhang H, Hong X, Ba X, Yu B, Wen X, Wang S, Wang X, Liu L, Xiao J. Asian J. Org. Chem. 2014; 3: 1168
136 Curiel D, Más-Montoya M, Usea L, Espinosa A, Orenes RA, Molina P. Org. Lett. 2012; 14: 3360
137 Qiu F, Zhang F, Tang R, Fu Y, Wang X, Han S, Zhuang X, Feng X. Org. Lett. 2016; 18: 1398
138 Squillaci M, Qiu F, Zhang F, Feng X, Samori P. Adv. Mater. 2016; 28: 5249
139 Stępień M, Gońka E, Żyła M, Sprutta N. Chem. Rev. 2017; 117: 3479
140 Takase M, Narita T, Fujita W, Asano MS, Nishinaga T, Benten H, Yoza K, Müllen K. J. Am. Chem. Soc. 2013; 135: 8031
141 Krieg M, Reicherter F, Haiss P, Ströbele M, Eichele K, Treanor M.-J, Schaub R, Bettinger HF. Angew. Chem. Int. Ed. 2015; 54: 8284
142 Lorenz T, Lik A, Plamper FA, Helten H. Angew. Chem. Int. Ed. 2016; 55: 7236
143 Hatakeyama T, Hashimoto S, Seki S, Nakamura M. J. Am. Chem. Soc. 2011; 133: 18614
144 Cai J, Pignedoli CA, Talirz L, Ruffieux P, Söde H, Liang L, Meunier V, Berger R, Li R, Feng X, Müllen K, Fasel R. Nat. Nanotechnol. 2014; 9: 896
145 Zhang Y, Zhang Y, Li G, Lu J, Lin X, Du S, Berger R, Feng X, Müllen K, Gao H.-J. Appl. Phys. Lett. 2014; 105: 023101