BN-embedded aromatics for optoelectronic applications
- Corresponding author: Jie-Yu Wang, semiconductors.jieyuwang@pku.edu.cn
Citation: Jie-Yu Wang, Jian Pei. BN-embedded aromatics for optoelectronic applications[J]. Chinese Chemical Letters, ;2016, 27(8): 1139-1146. doi: 10.1016/j.cclet.2016.06.014
(a) K. Takimiya, I. Osaka, M. Nakano, π-Building blocks for organic electronics: revaluation of "inductive" and "resonance" effects of π-electron deficient units, Chem. Mater. 26(2014) 587-593; (b) W.P. Wu, Y.Q. Liu, D.B. Zhu, π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications, Chem. Soc. Rev. 39(2010) 1489-1502; (c) L.T. Dou, J.B. You, Z.R. Hong, et al., 25th Anniversary article: a decade of organic/polymeric photovoltaic research, Adv. Mater. 25(2013) 6642-6671; (d) H. Usta, A. Facchetti, T.J. Marks, n-Channel semiconductor materials design for organic complementary circuits, Acc. Chem. Res. 44(2011) 501-510; (e) J.G. Mei, Y. Diao, A.L. Appleton, L. Fang, Z.N. Bao, Integrated materials design of organic semiconductors for field-effect transistors, J. Am. Chem. Soc. 135(2013) 6724-6746; (f) P.M. Beaujuge, J.M.J. Fréchet, Molecular design and ordering effects in pfunctional materials for transistor and solar cell applications, J. Am. Chem. Soc. 133(2011) 20009-20029; (g) C.L. Wang, H.L. Dong, W.P. Hu, Y.Q. Liu, D.B. Zhu, Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics, Chem. Rev. 112(2012) 2208-2267; (h) Z.T. Huang, C.C. Fan, G.B. Xue, et al., Solution-grown aligned crystals of diketopyrrolopyrroles (DPP)-based small molecules: rough surfaces and relatively low charge mobility, Chin. Chem. Lett. 27(2016) 523-526.
(a) W. Jiang, Y. Li, Z.H. Wang, Heteroarenes as high performance organic semiconductors, Chem. Soc. Rev. 42(2013) 6113-6127; (b) E.J. Wang, C.L. Wang, Q. Meng, et al., Syntheses of molecular wires containing redox center: reversible redox property and good energy level matching with Au electrode, Chin. Chem. Lett. 19(2008) 1285-1289; (c) B. Gao, Y. Li, H. Tian, Synthesis and near-infrared characteristics of novel perylenebisimide dyes bay-functionalized with naphthalimide chromophores, Chin. Chem. Lett. 18(2007) 283-286.
(a) M. Mas-Torrent, M. Durkut, P. Hadley, X. Ribas, C. Rovira, High mobility of dithiophene-tetrathiafulvalene single-crystal organic field effect transistors, J. Am. Chem. Soc. 126(2004) 984-985; (b) H. Ebata, T. Izawa, E. Miyazaki, et al., Highly soluble[1] benzothieno[32-b]benzothiophene (BTBT) derivatives for high-performance, solution-processed organic field-effect transistors, J. Am. Chem. Soc. 129(2007) 15732-15733.
M.J.S. Dewar, V.P. Kubba, R. Pettit. 624. New heteroaromatic compounds. Part I. 9-Aza-10-boraphenanthrene[J]. J. Chem. Soc, 1958:3073-3076. doi: 10.1039/jr9580003073
(a) M.J.S. Dewar, W.H. Poesche, New heteroaromatic compounds. XXI. Some tetracyclic systems 2, J. Org. Chem. 29(1964) 1757-1762; (b) M.J.S. Dewar, W.H. Poesche, New heteroaromaticcompounds. XVIII. Boron-containing analogs of benz[a]anthracene, J. Am. Chem. Soc. 85(1963) 2253-2256; (c) D.J.H. Emslie, W.E. Piers, M. Parvez, 2,2'-Diborabiphenyl: a Lewis acid analogue of 2,20-bipyridine, Angew. Chem. Int. Ed. 42(2003) 1252-1255; (d) C.A. Jaska, D.J.H. Emslie, M.J.D. Bosdet, et al., Triphenylene analogues with B2N2C2 cores: synthesis, structure, redox behavior, and photophysical properties, J. Am. Chem. Soc. 128(2006) 10885-10896.
(a) D.H. Knack, J.L. Marshall, G.P. Harlow, et al., BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues, Angew. Chem. Int. Ed. 52(2013) 2599-2601; (b) A.J. Ashe III, Aromatic borataheterocycles: surrogates for cyclopentadienyl in transition-metal complexes, Organometallics 28(2009) 4236-4248; (c) W. Luo, P.G. Campbell, L.N. Zakharov, S.Y. Liu, A single-component liquid-phase hydrogen storage material, J. Am. Chem. Soc. 133(2011) 19326-19329; (d) P.G. Campbell, L.N. Zakharov, D.J. Grant, D.A. Dixon, S.Y. Liu, Hydrogen storage by boron-nitrogen heterocycles: a simple route for spent fuel regeneration, J. Am. Chem. Soc. 132(2010) 3289-3291.
(a) M.J.D. Bosdet, W.E. Piers, T.S. Sorensen, M. Parvez, 10a-Aza-10b-borapyrenes: heterocyclic analogues of pyrene with internalized BN moieties, Angew. Chem. Int. Ed. 46(2007) 4940-4943; (b) X.Y. Wang, D.C. Yang, F.D. Zhuang, et al., Postfunctionalization of BN-embedded polycyclic aromatic compounds for fine-tuning of their molecular properties, Chem. Eur. J. 21(2015) 8867-8873.
(a) M.J.D. Bosdet, W.E. Piers, B-N as a C-C substitute in aromatic systems, Can. J. Chem. 87(2009) 8-29; (b) P.G. Campbell, A.J.V. Marwitz, S.Y. Liu, Recent advances in azaborinechemistry, Angew. Chem. Int. Ed. 51(2012) 6074-6092; (c) X.Y. Wang, J.Y. Wang, J. Pei, BN heterosuperbenzenes: synthesis and properties, Chem. Eur. J. 21(2015) 3528-3539.
G. Ulrich, R. Ziessel, A. Harriman. The chemistry of fluorescent bodipy dyes: versatility unsurpassed[J]. Angew. Chem. Int. Ed., 2008,47:1184-1201. doi: 10.1002/(ISSN)1521-3773
(a) D.M. Chen, Q. Qin, Z.B. Sun, Q. Peng, C.H. Zhao. Synthesis and properties of B,Nbridged p-terphenyls, Chem. Commun., 2014,50: 782-784; (b) D.M. Chen, S. Wang, H.X. Li, X.Z. Zhu, C.H. Zhao, Solid-state emissive B,Sbridged p-terphenyls: synthesis, properties, and utility as bifunctional fluorescent sensor for Hg2+ and F- ions[J]. Inorg. Chem., 2014,53:12532-12539. doi: 10.1021/ic502088k
T. Hatakeyama, S. Hashimoto, S. Seki, M. Nakamura. Synthesis of BN-fused polycyclic aromatics via tandemintramolecular electrophilic areneborylation[J]. J. Am. Chem. Soc., 2011,133:18614-18617. doi: 10.1021/ja208950c
T. Hatakeyama, S. Hashimoto, T. Oba, M. Nakamura. Azaboradibenzo[6] helicene: carrier inversion induced by helical homochirality[J]. J. Am. Chem. Soc., 2012,134:19600-19603. doi: 10.1021/ja310372f
X.Y. Wang, H.R. Lin, T. Lei. Azaborine compounds for organic field-effect transistors: efficient synthesis, remarkable stability, and BN dipole interactions[J]. Angew. Chem. Int. Ed., 2013,52:3117-3120. doi: 10.1002/anie.201209706
X.Y. Wang, F.D. Zhuang, X. Zhou. Influence of alkyl chain length on the solidstate properties and transistor performance of BN-substituted tetrathienonaphthalenes[J]. J. Mater. Chem. C, 2014,2:8152-8161. doi: 10.1039/C4TC01369G
X.Y. Wang, F.D. Zhuang, R.B. Wang. A straightforward strategy toward large BN-embedded π-systems: synthesis, structure, and optoelectronic properties of extended BN heterosuperbenzenes[J]. J. Am. Chem. Soc., 2014,136:3764-3767. doi: 10.1021/ja500117z
X.Y. Wang, F.D. Zhuang, J.Y. Wang, J. Pei. Incorporation of polycyclic azaborine compounds into polythiophene-type conjugated polymers for organic field-effect transistors[J]. Chem. Commun., 2015,51:17532-17535. doi: 10.1039/C5CC06927K
X.Y. Wang, F. Zhang, J. Liu. Ladder-type BN-embedded heteroacenes with blue emission[J]. Org. Lett., 2013,15:5714-5717. doi: 10.1021/ol402745r
(a) X.Y. Wang, F.D. Zhuang, X.C. Wang, et al., Synthesis, structure and properties of C3-symmetric heterosuperbenzene with three BN units, Chem. Commun. 51(2015) 4368-4371; (b) G. Li, W.W. Xiong, P.Y. Gu, et al., 15,9-Triaza-2,6,10-triphenylboracoronene: BN-embedded analogue of coronene, Org. Lett. 17(2015) 560-563.
S. Hashimoto, T. Ikuta, K. Shiren. Triplet-energy control of polycyclic aromatic hydrocarbons by BN replacement: development of ambipolar host materials for phosphorescent organic light-emitting diodes[J]. Chem. Mater., 2014,26:6265-6271. doi: 10.1021/cm503102d
D.L. Crossley, I.A. Cade, E.R. Clark. Enhancing electron affinity and tuning band gap in donor-acceptor organic semiconductors bybenzothiadiazole directed C-H borylation[J]. Chem. Sci., 2015,6:5144-5151. doi: 10.1039/C5SC01800E
T. Hatakeyama, K. Shiren, K. Nakajima. Ultrapure blue thermally activated delayed fluorescence molecules: efficient HOMO-LUMO separation by the multiple resonance effect[J]. Adv. Mater., 2016,28:2777-2781. doi: 10.1002/adma.v28.14
C.D. Dou, Z.C. Ding, Z.J. Zhang. Developing conjugated polymers with high electron affinity by replacing a C-C unit with a B←N unit[J]. Angew. Chem. Int. Ed., 2015,54:3648-3652. doi: 10.1002/anie.201411973
C.D. Dou, X.J. Long, Z.C. Ding. An electron-deficient building block based on the B←N unit: an electron acceptor for all-polymer solar cells[J]. Angew. Chem. Int. Ed., 2016,55:1436-1440. doi: 10.1002/anie.201508482
R.Y. Zhao, C.D. Dou, Z.Y. Xie, J. Liu, L.X. Wang. Polymer acceptor based on B←N units with enhanced electron mobility for efficient all-polymer solar cells[J]. Angew. Chem. Int. Ed., 2016,55:5313-5317. doi: 10.1002/anie.201601305
(a) J.S. Lu, S.B. Ko, N.R. Walters, et al., Formation of azaborines by photoelimination of B,N-heterocyclic compounds, Angew. Chem. Int. Ed. 52(2013) 4544-4548; (b) D.T. Yang, S.K. Mellerup, X. Wang, J.S. Lu, S.N. Wang, Reversible 1,1-hydroboration: boryl insertion into a C-N bond and competitive elimination of HBR2 or R-H, Angew. Chem. Int. Ed. 54(2015) 5498-5501; (c) Y.G. Shi, D.T. Yang, S.K. Mellerup, et al., 1,1-Hydroboration of fused azole-isoindole analogues as an approach for construction of B,N-heterocycles and azole-fused B,N-naphthalenes, Org. Lett. 18(2016) 1626-1629.
S.N. Wang, D.T. Yang, J.S. Lu. In situ solid-state generation of (BN)2-pyrenes and electroluminescent devices[J]. Angew. Chem. Int. Ed., 2015,54:15074-15078. doi: 10.1002/anie.201507770
(a) Y.L. Rao, H. Amarne, L.D. Chen, et al., Photo- and thermal-induced multistructural transformation of 2-phenylazolyl chelate boron compounds, J. Am. Chem. Soc. 135(2013) 3407-3410;(b) Y.L. Rao, C. Hörl, H. Braunschweig, S.N. Wang, Reversible photochemical and thermal isomerization of azaboratabisnorcaradiene to azaborabenzotropilidene, Angew. Chem. Int. Ed. 53(2014) 9086-9089.
M. Lepeltier, O. Lukoyanova, A. Jacobson, S. Jeeva, D.F. Perepichka. New azaborinethiopheneheteroacenes[J]. Chem. Commun., 2010,46:7007-7009. doi: 10.1039/c0cc01963a
(a) T. Agou, M. Sekine, J. Kobayashi, T. Kawashima, Multi-step detection of cyanide ion by a bis(dimesitylboryl)dibenzoazaborine, J. Organomet. Chem. 694(2009) 3833-3836; (b) T. Agou, M. Sekine, J. Kobayashi, T. Kawashima, Synthesis and reactivity of a bis(dimesitylboryl)azaborine and its fluoride sensing ability, Chem. Commun. (2009) 1894-1896.
T. Agou, M. Sekine, J. Kobayashi, T. Kawashima. Detection of biologically important anions in aqueous media by dicationic azaborines bearing ammonio or phosphonio groups[J]. Chem. Eur. J., 2009,15:5056-5062. doi: 10.1002/chem.v15:20
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