Charge transport and transfer phenomena involving conjugated acenes and heteroacenes
Source abstract
Abstract
Conjugated acenes are very promising for their applicability in different optoelectronic devices. In particular, pentacene (PCn) shows some distinct behaviours, namely high optical absorption and remarkably high carrier mobility which makes it as a landmark semiconductor for use in field-effect transistors or hole transporting materials in organic photovoltaics. During the last few decades, a large number of theoretical and experimental researches has been performed showing the practical applicability of different acenes and heteroatom-doped acenes (heteroacenes). Few reviews are also made in this regard. However, correlating the molecular properties arising from their intrinsic electronic structures with their charge transfer (CT) and transport characteristics is really scattered. Furthermore, very recent understandings on the nanojunctions made of acenes along with suitable electrodes need to be reviewed for further development of their performances in electronic devices. At the same time, the photovoltaic applicability of acenes and heteroacenes has recently been shown as an interplay of the dynamics of CT states as well as the intrinsic charge separation within the molecules or composites. The present review aims to point out those recent observations so as to draw more attention for further development in the area of acene- and heteroacene-based optoelectronic devices. We concentrate more on the structure–property relationships which could guide the device performance. As the subject area is so vast, we put emphasis on the very recent studies on PCn and some lower S,N-heteroacenes.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Organic Electronics and Photovoltaics · Molecular Junctions and Nanostructures · Quantum and electron transport phenomena
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (100+)
Show source-provided references
1. Duan C, Zhang K, Zhong C, Huang F and Cao Y 2013 Chem. Soc. Rev. 42 907110.1039/c3cs60200a ↗
2. Beaujuge P M and Fréchet J M 2011 J. Am. Chem. Soc. 133 2000910.1021/ja2073643 ↗
3. Facchetti A 2010 Chem. Mater. 23 73310.1021/cm102419z ↗
4. Wang C, Dong H, Hu W, Liu Y and Zhu D 2011 Chem. Rev. 112 220810.1021/cr100380z ↗
5. Tsai C H, Chirdon D N, Maurer A B, Bernhard S and Noonan K J 2013 Org. Lett. 15 523010.1021/ol4024024 ↗
6. Shinar J and Savvateev V 2004 Introduction to organic light-emitting devices (New York: Springer)10.1007/978-0-387-21720-8 ↗
7. Mei J, Diao Y, Appleton A L, Fang L and Bao Z 2013 J. Am. Chem. Soc. 135 672410.1021/ja400881n ↗
8. Watanabe M, Chang Y J, Liu S W, Chao T H, Goto K, Islam M M et al 2012 Nat. Chem. 4 57410.1038/nchem.1381 ↗
9. Anthony J E 2006 Chem. Rev. 106 502810.1021/cr050966z ↗
10. Goldmann C, Haas S, Krellner C, Pernstich K, Gundlach D and Batlogg B 2004 J. Appl. Phys. 96 208010.1063/1.1767292 ↗
11. Pramanik A, Mandal B, Sarkar S and Sarkar P 2014 Chem. Phys. Lett. 597 110.1016/j.cplett.2014.02.027 ↗
12. Lin Y Y, Gundlach D, Nelson S F and Jackson T N 1997 IEEE Trans. Electron Dev. 44 132510.1109/16.605476 ↗
13. Nelson S, Lin Y Y, Gundlach D and Jackson T 1998 Appl. Phys. Lett. 72 185410.1063/1.121205 ↗
14. Dimitrakopoulos C D and Malenfant P R 2002 Adv. Mater. 14 9910.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9 ↗
15. Chason M, Brazis P W, Zhang J, Kalyanasundaram K and Gamota D R 2005 Proc IEEE 93 134810.1109/JPROC.2005.850306 ↗
16. Yang H, Shin T J, Ling M M, Cho K, Ryu C Y and Bao Z 2005 J. Am. Chem. Soc. 127 1154210.1021/ja052478e ↗
17. Zu Heringdorf F J M, Reuter M and Tromp R 2001 Nature 412 51710.1038/35087532 ↗
18. Wen S H, Deng W Q and Han K L 2010 Phys. Chem. Chem. Phys. 12 926710.1039/b923862j ↗
19. Pshenichnyuk I A, Coto P B, Leitherer S and Thoss M 2013 J. Phys. Chem. Lett. 4 80910.1021/jz400025q ↗
20. Kast H, Mishra A, Schulz G L, Urdanpilleta M, Mena-Osteritz E and Bäuerle P 2015 Adv. Funct. Mater. 25 341410.1002/adfm.201500565 ↗
21. Kihira Y, Shimada T, Matsuo Y, Nakamura E and Hasegawa T 2009 Nano Lett. 9 144210.1021/nl803284t ↗
22. Kim W K and Lee J L 2006 Appl. Phys. Lett. 88 26210210.1063/1.2218044 ↗
23. Ihm K, Kim B, Kang T H, Kim K J, Joo M H, Kim T H et al 2006 Appl. Phys. Lett. 89 03350410.1063/1.2227712 ↗
24. Amy F, Chan C and Kahn A 2005 Org. Electron. 6 8510.1016/j.orgel.2005.03.003 ↗
25. Han M Y, Özyilmaz B, Zhang Y and Kim P 2007 Phys. Rev. Lett. 98 20680510.1103/PhysRevLett.98.206805 ↗
26. Chen Z, Lin Y M, Rooks M J and Avouris P 2007 Physica E 40 22810.1016/j.physe.2007.06.020 ↗
27. Li X, Wang X, Zhang L, Lee S and Dai H 2008 Science 319 122910.1126/science.1150878 ↗
28. Jin C, Lan H, Peng L, Suenaga K and Iijima S 2009 Phys. Rev. Lett. 102 20550110.1103/PhysRevLett.102.205501 ↗
29. Cao Y, Liu S, Shen Q, Yan K, Li P, Xu J et al 2009 Adv. Funct. Mater. 19 274310.1002/adfm.200900408 ↗
30. Prins F, Monrabal-Capilla M, Osorio E A, Coronado E and van der Zant H S 2011 Adv. Mater. 23 154510.1002/adma.201003821 ↗
31. Di C A, Wei D, Yu G, Liu Y, Guo Y and Zhu D 2008 Adv. Mater. 20 328910.1002/adma.200800150 ↗
32. Lee C G, Park S, Ruoff R S and Dodabalapur A 2009 Appl. Phys. Lett. 95 188
33. Liu W, Jackson B L, Zhu J, Miao C Q, Chung C H, Park Y J et al 2010 ACS Nano 4 392710.1021/nn100728p ↗
34. Wakabayashi K 2001 Phys. Rev. B 64 12542810.1103/PhysRevB.64.125428 ↗
35. Sasaki K I, Murakami S and Saito R 2006 Appl. Phys. Lett. 88 11311010.1063/1.2181274 ↗
36. Son Y W, Cohen M L and Louie S G 2006 Nature 444 34710.1038/nature05180 ↗
37. Son Y W, Cohen M L and Louie S G 2006 Phys. Rev. Lett. 97 21680310.1103/PhysRevLett.97.216803 ↗
38. Hod O, Barone V, Peralta J E and Scuseria G E 2007 Nano Lett. 7 229510.1021/nl0708922 ↗
39. Rudberg E, Sałek P and Luo Y 2007 Nano Lett. 7 221110.1021/nl070593c ↗
40. Nakada K, Fujita M, Dresselhaus G and Dresselhaus M S 1996 Phys. Rev. B 54 1795410.1103/PhysRevB.54.17954 ↗
41. Joly V J, Kiguchi M, Hao S J, Takai K, Enoki T, Sumii R et al 2010 Phys. Rev. B 81 24542810.1103/PhysRevB.81.245428 ↗
42. Topsakal M, Sevinçli H and Ciraci S 2008 Appl. Phys. Lett. 92 17311810.1063/1.2919525 ↗
43. Zheng J, Yan X, Yu L, Li H, Qin R, Luo G et al 2011 J. Phys. Chem. C 115 854710.1021/jp200982w ↗
44. Kang J, Wu F and Li J 2011 Appl. Phys. Lett. 98 08310910.1063/1.3559001 ↗
45. Zeng H, Zhao J, Wei J and Hu H 2011 Eur. Phys. J. B 79 33510.1140/epjb/e2010-10725-4 ↗
46. Zeng M, Shen L, Yang M, Zhang C and Feng Y 2011 Appl. Phys. Lett. 98 05310110.1063/1.3549154 ↗
47. Mandal B, Sarkar S, Pramanik A and Sarkar P 2013 J. Appl. Phys. 114 17370110.1063/1.4828733 ↗
48. Sarkar S, Pramanik A and Sarkar P 2016 Chem. Phys. 478 17310.1016/j.chemphys.2016.03.012 ↗
49. Mandal B, Sarkar S, Pramanik A and Sarkar P 2013 Phys. Chem. Chem. Phys. 15 2100110.1039/c3cp53390e ↗
50. Mandal B, Sarkar S, Pramanik A and Sarkar P 2012 J. Appl. Phys. 112 11371010.1063/1.4768524 ↗
51. Pramanik A, Sarkar S and Sarkar P 2012 J. Phys. Chem. C 116 1806410.1021/jp304582k ↗
52. Modarresi M, Roknabadi M and Shahtahmasbi N 2011 Physica E 43 175110.1016/j.physe.2011.06.006 ↗
53. Saffarzadeh A and Farghadan R 2011 Appl. Phys. Lett. 98 02310610.1063/1.3537965 ↗
54. Song Y, Xie Z, Ma Y, Li Z and Wang C K 2014 J. Phys. Chem. C 118 1871310.1021/jp504448n ↗
55. Kang H S and Pramanik A 2011 J. Chem. Phys. 135 12470810.1063/1.3643337 ↗
56. Mandal B, Sarkar S, Pramanik A and Sarkar P 2014 RSC Adv. 4 4994610.1039/C4RA08677E ↗
57. Mishra A, Popovic D, Vogt A, Kast H, Leitner T, Walzer K et al 2014 Adv. Mater. 26 721710.1002/adma.201402448 ↗
58. Qin P, Kast H, Nazeeruddin M K, Zakeeruddin S M, Mishra A, Bäuerle P et al 2014 Energy Environ. Sci. 7 298110.1039/C4EE01220H ↗
59. Wetzel C, Mishra A, Mena-Osteritz E, Liess A, Stolte M, Würthner F et al 2013 Org. Lett. 16 36210.1021/ol403153z ↗
60. Wetzel C, Brier E, Vogt A, Mishra A, Mena-Osteritz E and Bäuerle P 2015 Angew. Chem. Int. Ed. 54 1233410.1002/anie.201502840 ↗
61. Aragó J, Viruela P M, Ortí E, Malavé Osuna R, Vercelli B, Zotti G et al 2010 Chemistry 16 548110.1002/chem.200903343 ↗
62. Osaka I, Zhang R, Sauvé G, Smilgies D M, Kowalewski T and McCullough R D 2009 J. Am. Chem. Soc. 131 252110.1021/ja801475h ↗
63. Quinn J T, Zhu J, Li X, Wang J and Li Y 2017 J. Mater. Chem. C 5 865410.1039/C7TC01680H ↗
64. Zaumseil J and Sirringhaus H 2007 Chem. Rev. 107 129610.1021/cr0501543 ↗
65. Yan H, Chen Z, Zheng Y, Newman C, Quinn J R, Dötz F et al 2009 Nature 457 67910.1038/nature07727 ↗
66. Dhondge A P, Chen J Y, Lin T, Yen F M, Li K W, Hsieh H C et al 2018 Org. Lett. 20 4010.1021/acs.orglett.7b03284 ↗
67. Cochran J E, Amir E, Sivanandan K, Ku S Y, Seo J H, Collins B A et al 2013 J. Polym. Sci. B: Polym. Phys. 51 4810.1002/polb.23167 ↗
68. Facchetti A, Yoon M H, Stern C L, Katz H E and Marks T J 2003 Angew. Chem. Int. Ed. 42 390010.1002/anie.200351253 ↗
69. Pramanik A and Sarkar P 2015 Phys. Chem. Chem. Phys. 17 2670310.1039/C5CP03425F ↗
70. Gryn’ova G, Ollitrault P J and Corminboeuf C 2017 Phys. Chem. Chem. Phys. 19 2325410.1039/C7CP04295G ↗
71. Ando S, Nishida J I, Fujiwara E, Tada H, Inoue Y, Tokito S et al 2005 Chem. Mater. 17 126110.1021/cm0478632 ↗
72. Melucci M, Frere P, Allain M, Levillain E, Barbarella G and Roncali J 2007 Tetrahedron 63 977410.1016/j.tet.2007.07.006 ↗
73. Su T A, Li H, Steigerwald M L, Venkataraman L and Nuckolls C 2015 Nat. Chem. 7 21510.1038/nchem.2180 ↗
74. Pramanik A and Sarkar P 2015 J. Chem. Phys. 143 11431410.1063/1.4931400 ↗
75. Dell E J and Campos L M 2012 J. Mater. Chem. 22 1294510.1039/c2jm31220d ↗
76. Dell E J, Capozzi B, Xia J, Venkataraman L and Campos L M 2015 Nat. Chem. 7 20910.1038/nchem.2160 ↗
77. Capozzi B, Xia J, Adak O, Dell E J, Liu Z F, Taylor J C et al 2015 Nat. Nanotechnol. 10 52210.1038/nnano.2015.97 ↗
78. Tang M L, Reichardt A D, Wei P and Bao Z 2009 J. Am. Chem. Soc. 131 526410.1021/ja809659b ↗
79. Simbeck A J, Qian G, Nayak S K, Wang G C and Lewis K M 2012 Surf. Sci. 606 141210.1016/j.susc.2012.05.001 ↗
80. Xu B and Tao N J 2003 Science 301 122110.1126/science.1087481 ↗
81. Blum A S, Yang J C, Shashidhar R and Ratna B 2003 Appl. Phys. Lett. 82 332210.1063/1.1573365 ↗
82. Pramanik C, Li Y, Singh A, Lin W, Hodgson J L, Briggs J B et al 2013 J. Mater. Chem. C 1 219310.1039/c3tc00278k ↗
83. Yoo S, Domercq B and Kippelen B 2004 Appl. Phys. Lett. 85 542710.1063/1.1829777 ↗
84. Pramanik A, Sarkar S, Pal S and Sarkar P 2015 Phys. Lett. A 379 103610.1016/j.physleta.2015.01.040 ↗
85. Biswas S, Pramanik A, Pal S and Sarkar P 2017 J. Phys. Chem. C 121 257410.1021/acs.jpcc.6b11471 ↗
86. Ostroverkhova O, Shcherbyna S, Cooke D G, Egerton R F, Hegmann F A, Tykwinski R R et al 2005 J. Appl. Phys. 98 03370110.1063/1.1949711 ↗
87. Mishra A and Bäuerle P 2012 Angew. Chem. Int. Ed. 51 202010.1002/anie.201102326 ↗
88. Malytskyi V, Simon J J, Patrone L and Raimundo J M 2015 RSC Adv. 5 35410.1039/C4RA11664J ↗
89. Fitzner R, Mena-Osteritz E, Mishra A, Schulz G, Reinold E, Weil M et al 2012 J. Am. Chem. Soc. 134 1106410.1021/ja302320c ↗
90. Chen Y, Wan X and Long G 2013 Acc. Chem. Res. 46 264510.1021/ar400088c ↗
91. Wu J S, Cheng Y J, Lin T Y, Chang C Y, Shih P I and Hsu C S 2012 Adv. Funct. Mater. 22 171110.1002/adfm.201102906 ↗
92. Mitsudo K, Shimohara S, Mizoguchi J, Mandai H and Suga S 2012 Org. Lett. 14 270210.1021/ol300887t ↗
93. Chung C L, Chen C Y, Kang H W, Lin H W, Tsai W L, Hsu C C et al 2016 Org. Electron. 28 22910.1016/j.orgel.2015.10.030 ↗
94. Chung C L, Chen C H, Tsai C H and Wong K T 2015 Org. Electron. 18 810.1016/j.orgel.2015.01.005 ↗
95. Lee H, Jo H, Kim D, Biswas S, Sharma G D and Ko J 2016 Dyes Pigm. 129 20910.1016/j.dyepig.2016.02.029 ↗
96. Wetzel C, Mishra A, Mena-Osteritz E, Walzer K, Pfeiffer M and Bäuerle P 2016 J. Mater. Chem. C 4 371510.1039/C5TC03539B ↗
97. O’regan B and Grätzel M 1991 Nature 353 73710.1038/353737a0 ↗
98. Tachibana Y, Hara K, Sayama K and Arakawa H 2002 Chem. Mater. 14 252710.1021/cm011563s ↗
99. Rehm J M, McLendon G L, Nagasawa Y, Yoshihara K, Moser J and Grätzel M 1996 J. Phys. Chem. 100 957710.1021/jp960155m ↗
100. Kitamura T, Ikeda M, Shigaki K, Inoue T, Anderson N A, Ai X et al 2004 Chem. Mater. 16 180610.1021/cm0349708 ↗