Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

被引:916
作者
Stepien, Marcin [1 ]
Gonka, Elzbieta [1 ]
Zyla, Marika [1 ]
Sprutta, Natasza [1 ]
机构
[1] Uniwersytet Wroclawski, Wydzial Chem, Ul F Joliot Curie 14, PL-50383 Wroclaw, Poland
关键词
CARCINOGENIC NITROGEN-COMPOUNDS; N-FUSED PORPHYRIN; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; MAGNETIC CIRCULAR-DICHROISM; DINUCLEAR RUTHENIUM COMPLEX; DENSITY-FUNCTIONAL THEORY; LIGHT-EMITTING-DIODES; PI-PI STACKING; ANTIAROMATIC PLANAR CYCLOOCTATETRAENE;
D O I
10.1021/acs.chemrev.6b00076
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.
引用
收藏
页码:3479 / 3716
页数:238
相关论文
共 1630 条
[1]   STUDIES ON HETEROCYCLIC-ANALOGS OF AZULENES .11. SYNTHESES AND CYCLO-ADDITIONS OF CYCLOHEPTA[4,5]PYRROLO[1,2-A]IMIDAZOLES AND CYCLOHEPT[D]IMIDAZO[1,2-A]IMIDAZOLES [J].
ABE, N ;
NISHIWAKI, T ;
YAMAMOTO, H ;
KUNISHIGE, N .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (12) :3703-3714
[2]  
ACHESON RM, 1958, J CHEM SOC, P3750
[3]   ARYLATION REACTION OF CYCLIC GUANIDINE-ANALOGS WITH ALPHA-HALO-ANTHRAQUINONES - NEW ANTHRAPYRIMIDINES [J].
ADAM, JM ;
WINKLER, T ;
RIHS, G .
HELVETICA CHIMICA ACTA, 1982, 65 (07) :2318-2325
[4]   SYNTHESIS, SPONTANEOUS RACEMIZATION, AND PHOTOISOMERIZATION OF BENZO[E]PYRENE 9, 10-OXIDE [J].
AGARWAL, SK ;
BOYD, DR ;
DUNLOP, R ;
JENNINGS, WB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (11) :3013-3018
[5]  
Aggarwal AV, 2013, NAT CHEM, V5, P964, DOI [10.1038/nchem.1758, 10.1038/NCHEM.1758]
[6]   Relationship between two-photon absorption and the π-conjugation pathway in porphyrin arrays through dihedral angle control [J].
Ahn, TK ;
Kim, KS ;
Kim, DY ;
Noh, SB ;
Aratani, N ;
Ikeda, C ;
Osuka, A ;
Kim, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1700-1704
[7]  
Aihara H, 2001, ANGEW CHEM INT EDIT, V40, P3439, DOI 10.1002/1521-3773(20010917)40:18<3439::AID-ANIE3439>3.0.CO
[8]  
2-Z
[9]   Dithieno[3,4-b:3′,4′-d]thiophene-Annelated Antiaromatic Planar Cyclooctatetraene with Olefinic Protons [J].
Aita, Kazunari ;
Ohmae, Takeshi ;
Takase, Masayoshi ;
Nomura, Kotohiro ;
Kimura, Hideaki ;
Nishinage, Tohru .
ORGANIC LETTERS, 2013, 15 (14) :3522-3525
[10]   Expansion of a Pyrrole in meso-Tetraphenylporphyrin to a Pyrazine Imide Moiety Using a Beckmann Rearrangement [J].
Akhigbe, Joshua ;
Brueckner, Christian .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (18) :3876-3884