SCOPUS 정보 검색 플랫폼

Chemical Science

Volumn 2, Issue 12, 2011, Pages 2402-2406

Vapochromic and semiconducting solids of a bifunctional hydrocarbon

(4) Xia, Hai a Liu, Danqing a Song, Kesheng b Miao, Qian a

a CHINESE UNIVERSITY OF HONG KONG (Hong Kong)

b SOUTH CHINA NORMAL UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL MATERIALS; HYDRATES; MOLECULES; TOLUENE;

ANTI CONFORMERS; BIFUNCTIONAL; C-C DOUBLE BONDS; CONJUGATED MOLECULES; CUMULENES; CYCLOHEPTATRIENES; FIELD-EFFECT MOBILITIES; HIGH SELECTIVITY; IN-BUILDINGS; M-XYLENE; ORGANIC FUNCTIONAL MATERIALS; P TYPE SEMICONDUCTOR; SEMICONDUCTING SOLIDS; SYN CONFORMERS; VAPOCHROMIC BEHAVIOR; VOLATILE MOLECULES;

HYDROCARBONS;

EID: 84865407815 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c1sc00494h Document Type: Article

Times cited : (27)

References (53)

1
- 84871844821
- Hybrid solids consisting of the conducting layers of organic donor molecules and the magnetic layers of inorganic anions have been reported as bifunctional organic materials. For examples, see
- Hybrid solids consisting of the conducting layers of organic donor molecules and the magnetic layers of inorganic anions have been reported as bifunctional organic materials. For examples, see

2
- 6444237607
- M. Kurmoo A. W. Graham P. Day S. J. Coles M. B. Hursthouse J. L. Caulfield J. Singleton F. L. Pratt W. Hayes L. Ducasse P. Guionneau J. Am. Chem. Soc. 1995 117 12209 12217
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 12209-12217
- Kurmoo, M.¹ Graham, A.W.² Day, P.³ Coles, S.J.⁴ Hursthouse, M.B.⁵ Caulfield, J.L.⁶ Singleton, J.⁷ Pratt, F.L.⁸ Hayes, W.⁹ Ducasse, L.¹⁰ Guionneau, P.¹¹

3
- 0034706913
- E. Coronado J. R. Galán-Mascarós C. J. Gómez- García V. N. Laukhin Nature 2000 408 447 449
- (2000) Nature , vol.408 , pp. 447-449
- Coronado, E.¹ Galán-Mascarós, J.R.² Gómez-García, C.J.³ Laukhin, V.N.⁴

4
- 0037134911
- H. Fujiwara H. Kobayashi E. Fujiwara A. Kobayashi J. Am. Chem. Soc. 2002 124 6816 6817
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 6816-6817
- Fujiwara, H.¹ Kobayashi, H.² Fujiwara, E.³ Kobayashi, A.⁴

5
- 44949260124
- N. D. Kushch E. B. Yagubskii M. V. Kartsovnik L. I. Buravov A. D. Dubrovskii A. N. Chekhlov W. Biberacher J. Am. Chem. Soc. 2008 130 7238 7240
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 7238-7240
- Kushch, N.D.¹ Yagubskii, E.B.² Kartsovnik, M.V.³ Buravov, L.I.⁴ Dubrovskii, A.D.⁵ Chekhlov, A.N.⁶ Biberacher, W.⁷

6
- 77951176800
- E. Takahashi H. Takaya T. Naota Chem. Eur. J. 2010 16 4793 4802
- (2010) Chem. Eur. J. , vol.16 , pp. 4793-4802
- Takahashi, E.¹ Takaya, H.² Naota, T.³

7
- 0002591381
- C. L. Exstrom J. R. Sowa, Jr. C. A. Daws D. Janzen K. R. Mann G. A. Moore F. F. Stewart Chem. Mater. 1995 7 15 17
- (1995) Chem. Mater. , vol.7 , pp. 15-17
- Exstrom, C.L.¹ Sowa, Jr.J.R.² Daws, C.A.³ Janzen, D.⁴ Mann, K.R.⁵ Moore, G.A.⁶ Stewart, F.F.⁷

8
- 0032511389
- C. E. Buss C. E. Anderson M. K. Pomije C. M. Lutz D. Britton K. R. Mann J. Am. Chem. Soc. 1998 120 7783 7790
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 7783-7790
- Buss, C.E.¹ Anderson, C.E.² Pomije, M.K.³ Lutz, C.M.⁴ Britton, D.⁵ Mann, K.R.⁶

9
- 0037065686
- C. E. Buss K. R. Mann J. Am. Chem. Soc. 2002 124 1031 1039
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 1031-1039
- Buss, C.E.¹ Mann, K.R.²

10
- 0037008976
- M. Kato A. Omura A. Toshikawa S. Kishi Y. Sugimoto Angew. Chem. Int. Ed. 2002 41 3183 3185
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3183-3185
- Kato, M.¹ Omura, A.² Toshikawa, A.³ Kishi, S.⁴ Sugimoto, Y.⁵

11
- 1242269285
- L. J. Grove J. M. Rennekamp H. Jude W. B. Connick J. Am. Chem. Soc. 2004 126 1594 1595
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 1594-1595
- Grove, L.J.¹ Rennekamp, J.M.² Jude, H.³ Connick, W.B.⁴

12
- 11244321699
- T. J. Wadas Q.-M. Wang Y.-J. Kim C. Flaschenreim T. N. Blanton R. Eisenberg J. Am. Chem. Soc. 2004 126 16841 16849
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 16841-16849
- Wadas, T.J.¹ Wang, Q.-M.² Kim, Y.-J.³ Flaschenreim, C.⁴ Blanton, T.N.⁵ Eisenberg, R.⁶

13
- 0001745241
- M. A. Mansour W. B. Connick R. J. Lachicotte H. J. Gysling R. Eisenberg J. Am. Chem. Soc. 1998 120 1329 1330
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 1329-1330
- Mansour, M.A.¹ Connick, W.B.² Lachicotte, R.J.³ Gysling, H.J.⁴ Eisenberg, R.⁵

14
- 0035802328
- M. A. Rawashdeh-Omary M. A. Omary J. P. Fackler, Jr. R. Galassi B. R. Pietroni A. Burini J. Am. Chem. Soc. 2001 123 9689 9691
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9689-9691
- Rawashdeh-Omary, M.A.¹ Omary, M.A.² Fackler, Jr.J.P.³ Galassi, R.⁴ Pietroni, B.R.⁵ Burini, A.⁶

15
- 0037466983
- E. J. Fernández J. M. López-de-Luzuriaga M. Monge M. E. Olmos J. Pérez A. Laguna A. A. Mohamed J. P. Fackler, Jr. J. Am. Chem. Soc. 2003 125 2022 2023
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 2022-2023
- Fernández, E.J.¹ López-De-Luzuriaga, J.M.² Monge, M.³ Olmos, M.E.⁴ Pérez, J.⁵ Laguna, A.⁶ Mohamed, A.A.⁷ Fackler, Jr.J.P.⁸

16
- 10344243013
- J. Lefebvre R. J. Batchelor D. B. Leznoff J. Am. Chem. Soc. 2004 126 16117 16125
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 16117-16125
- Lefebvre, J.¹ Batchelor, R.J.² Leznoff, D.B.³

17
- 77955829260
- C. E. Strasser V. J. Catalano J. Am. Chem. Soc. 2010 132 10009 10011
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 10009-10011
- Strasser, C.E.¹ Catalano, V.J.²

18
- 0034728555
- L. G. Beauvais M. P. Shores J. R. Long J. Am. Chem. Soc. 2000 122 2763 2772
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 2763-2772
- Beauvais, L.G.¹ Shores, M.P.² Long, J.R.³

19
- 52949121362
- To the best of our knowledge, there are only two reports on vapochromic metal-free organic crystals. See: ref. 2
- E. J. Fernández J. M. López-de-Luzuriaga M. Monge M. E. Olmos R. C. Puelles A. Laguna A. A. Mohamed J. P. Fackler, Jr. Inorg. Chem. 2008 47 8069 8076
- (2008) Inorg. Chem. , vol.47 , pp. 8069-8076
- Fernández, E.J.¹ López-De-Luzuriaga, J.M.² Monge, M.³ Olmos, M.E.⁴ Puelles, R.C.⁵ Laguna, A.⁶ Mohamed, A.A.⁷ Fackler, Jr.J.P.⁸

20
- 79952794701
- C. Dou L. Han S. Zhao H. Zhang Y. Wang J. Phys. Chem. Lett. 2011 2 666 670
- (2011) J. Phys. Chem. Lett. , vol.2 , pp. 666-670
- Dou, C.¹ Han, L.² Zhao, S.³ Zhang, H.⁴ Wang, Y.⁵

21
- 2342486652
- S. R. Forrest Nature 2004 428 911 918
- (2004) Nature , vol.428 , pp. 911-918
- Forrest, S.R.¹

22
- 57549094328
- ed., WIley-VCH, Weinheim
- Organic Electronics: Materials, Manufacturing and Applications, ed., H. Klauk, WIley-VCH, Weinheim, 2006
- (2006) Organic Electronics: Materials, Manufacturing and Applications
- Klauk, H.¹

23
- 70350056098
- ed., WIley-VCH, Weinheim, For very limited examples of organic functional materials containing cycloheptatriene as building blocks, see
- Organic Photovoltaics: Materials, Device Physics and Manufacturing Techonologies, ed., C. Brabec, U. Scherf, and, V. Dyakonov, WIley-VCH, Weinheim, 2008
- (2008) Organic Photovoltaics: Materials, Device Physics and Manufacturing Techonologies
- Brabec, C.¹ Scherf, U.² Dyakonov, V.³

24
- 77950248976
- W. C. Chen Y. W. Lee C. T. Chen Org. Lett. 2010 12 1472 1475
- (2010) Org. Lett. , vol.12 , pp. 1472-1475
- Chen, W.C.¹ Lee, Y.W.² Chen, C.T.³

25
- 67650523628
- Y. Wei S. Samori S. Tojo M. Fujitsuka J. S. Lin C. T. Chen T. Majima J. Am. Chem. Soc. 2009 131 6698 6707
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6698-6707
- Wei, Y.¹ Samori, S.² Tojo, S.³ Fujitsuka, M.⁴ Lin, J.S.⁵ Chen, C.T.⁶ Majima, T.⁷

26
- 0000189651
- A. D. Becke J. Chem. Phys. 1993 98 5648 5652
- (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
- Becke, A.D.¹

27
- 0038596731
- B. Miehlich A. Savin H. Stoll H. Preuss Chem. Phys. Lett. 1989 157 200 206
- (1989) Chem. Phys. Lett. , vol.157 , pp. 200-206
- Miehlich, B.¹ Savin, A.² Stoll, H.³ Preuss, H.⁴

28
- 0345491105
- C. Lee W. Yang G. Parr Phys. Rev. B 1988 37 785 789
- (1988) Phys. Rev. B , vol.37 , pp. 785-789
- Lee, C.¹ Yang, W.² Parr, G.³

29
- 48749097043
- The crystals were completely dried under vacuum at room temperature and dissolved in CD2Cl2 before characterization by ¹H NMR spectroscopy Intermolecular carbon-carbon contacts within the range of 3.5 to 3.92 Å were considered as short contacts between neighboring pentacene molecules in crystals, see
- B. J. Dahl N. S. Mills J. Am. Chem. Soc. 2008 130 10179 10186
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 10179-10186
- Dahl, B.J.¹ Mills, N.S.²

30
- 0035805312
- Clathrates are also known as lattice inclusion compounds. For reviews, see
- T. Siegrist C. Kloc J. H. Schön B. Ballogg R. C. Haddon S. Berg G. A. Thomas Angew. Chem., Int. Ed. 2001 40 1732 1736
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1732-1736
- Siegrist, T.¹ Kloc, C.² Schön, J.H.³ Ballogg, B.⁴ Haddon, R.C.⁵ Berg, S.⁶ Thomas, G.A.⁷

31
- 0004260535
- WIley, Chichester, ch. 5
- J. W. Steed and J. L. Atwood, Supramolecular Chemistry, WIley, Chichester, 2000, ch. 5
- (2000) Supramolecular Chemistry
- Steed, J.W.¹ Atwood, J.L.²

32
- 0002896625
- R. Bishop Chem. Soc. Rev. 1996 25 311 320
- (1996) Chem. Soc. Rev. , vol.25 , pp. 311-320
- Bishop, R.¹

33
- 0035742937
- Three of the short contacts are between a benzene ring of one molecule and the central cumulene carbon atoms of its neighbor, and one short contact is between two nearest benzene rings
- F. Toda Pure Appl. Chem. 2001 73 1137 1145
- (2001) Pure Appl. Chem. , vol.73 , pp. 1137-1145
- Toda, F.¹

34
- 84954326629
- ed. E. R. T. Tiekink and J. J. Vittal, WIley, Chichester, 135-155 To measure UV-vis absorption spectra from the solids, a quartz plate was coated with fine crystalline powders of syn- and 3(anti- 1)·m-xylene, which were grown from ethyl acetate and m-xylene respectively
- M. J. Hardie, in Frontiers in Crystal Engineering, ed., E. R. T. Tiekink, and, J. J. Vittal, WIley, Chichester, 2006, pp. 135-155
- (2006) Frontiers in Crystal Engineering , vol.1
- Hardie, M.J.¹

35
- 0032486349
- U. Rohr P. Schilichting A. Böhm M. Gross K. Meerholz C. Bräuchle K. Müllen Angew. Chem., Int. Ed. 1998 37 1434 1437
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1434-1437
- Rohr, U.¹ Schilichting, P.² Böhm, A.³ Gross, M.⁴ Meerholz, K.⁵ Bräuchle, C.⁶ Müllen, K.⁷

36
- 31944440134
- Q. Miao X. Chi S. Xiao R. Zeiss M. Lefenfeld C. Kloc M. L. Steigerwald T. Siegrist C. Nuckolls J. Am. Chem. Soc. 2006 128 1340 1345
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 1340-1345
- Miao, Q.¹ Chi, X.² Xiao, S.³ Zeiss, R.⁴ Lefenfeld, M.⁵ Kloc, C.⁶ Steigerwald, M.L.⁷ Siegrist, T.⁸ Nuckolls, C.⁹

37
- 2142649256
- S.-H. Lim T. G. Bjorklund F. C. Spano C. J. Bardeen Phys. Rev. Lett. 2004 92 107402
- (2004) Phys. Rev. Lett. , vol.92 , pp. 107402
- Lim, S.-H.¹ Bjorklund, T.G.² Spano, F.C.³ Bardeen, C.J.⁴

38
- 0038035472
- G. A. Petersson M. A. Al-Laham J. Chem. Phys. 1991 94 6081 6090
- (1991) J. Chem. Phys. , vol.94 , pp. 6081-6090
- Petersson, G.A.¹ Al-Laham, M.A.²

39
- 36549091806
- G. A. Petersson A. Bennett T. G. Tensfeldt M. A. Al-Laham W. A. Shirley J. Mantzaris J. Chem. Phys. 1988 89 2193 2218
- (1988) J. Chem. Phys. , vol.89 , pp. 2193-2218
- Petersson, G.A.¹ Bennett, A.² Tensfeldt, T.G.³ Al-Laham, M.A.⁴ Shirley, W.A.⁵ Mantzaris, J.⁶

40
- 78651380354
- For ¹H NMR spectra, see the ESI In order of decreasing value, the saturated vapor pressures of benzene, toluene, p-xylene, m-xylene, bromobenzene, mesitylene, o-bromotoluene and o-dibromobenzene at 25 °C are 100.92, 27.71, 7.94, 7.61, 4.12, 2.32, 1.2 and 0.13 mmHg respectively. (The values of saturated vapor pressures are cited from)
- J. T. A. Jones D. Holden T. Mitra T. Hasell D. J. Adams K. E. Jelfs A. Trewin D. J. Willock G. M. Day J. Bacsa A. Steiner A. I. Cooper Angew. Chem. Int. Ed. 2011 50 749 753
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 749-753
- Jones, J.T.A.¹ Holden, D.² Mitra, T.³ Hasell, T.⁴ Adams, D.J.⁵ Jelfs, K.E.⁶ Trewin, A.⁷ Willock, D.J.⁸ Day, G.M.⁹ Bacsa, J.¹⁰ Steiner, A.¹¹ Cooper, A.I.¹²

41
- 84871841623
- Several metal complexes are also reported to (partially) owe their vapochromic behaviors to changes of π-π interactions in response to organic vapors. For examples, see
- Several metal complexes are also reported to (partially) owe their vapochromic behaviors to changes of π-π interactions in response to organic vapors. For examples, see

42
- 0035844918
- W. Lu M. C. W. Chan K.-K. Cheung C.-M. Che Organometallics 2001 20 2477 2486
- (2001) Organometallics , vol.20 , pp. 2477-2486
- Lu, W.¹ Chan, M.C.W.² Cheung, K.-K.³ Che, C.-M.⁴

43
- 52949093854
- Z. Liu Z. Bian J. Bian Z. Li D. Nie C. Huang Inorg. Chem. 2008 47 8025 8030
- (2008) Inorg. Chem. , vol.47 , pp. 8025-8030
- Liu, Z.¹ Bian, Z.² Bian, J.³ Li, Z.⁴ Nie, D.⁵ Huang, C.⁶

44
- 78049389951
- The vapochromic metal-free organic crystals reported in ref. 2 involve guest-induced change of π-donor/acceptor interactions The cyclic voltammogram (CV) of 1 (shown in the ESI) in CH2Cl2 exhibits one pseudo-reversible oxidation wave with a half-wave oxidation potential vs. ferrocenium/ferrocene of 0.42 V, from which the HOMO energy level of 1 is estimated as -5.22 eV, in agreement with the calculated value
- A. Kobayashi M.-a. Dosen M. Chang K. Nakajima S.-i. Noro M. Kato J. Am. Chem. Soc. 2010 132 15286 15298
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15286-15298
- Kobayashi, A.¹ Dosen, M.-A.² Chang, M.³ Nakajima, K.⁴ Noro, S.-I.⁵ Kato, M.⁶

45
- 0034873221
- To the best of our knowledge, there are no reported examples for organic semiconductors containing cumulene moieties, and there is only one precedent for organic semiconductors containing cycloheptatriene subunits. See: ref. 7b
- H. E. Katz Z. Bao S. L. Gilat Acc. Chem. Res. 2001 34 359 369
- (2001) Acc. Chem. Res. , vol.34 , pp. 359-369
- Katz, H.E.¹ Bao, Z.² Gilat, S.L.³

46
- 67649995543
- Y. Ito A. A. Virkar S. Mannsfeld J. H. Oh M. Toney A. Locklin Z. Bao J. Am. Chem. Soc. 2009 131 9396 9404
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 9396-9404
- Ito, Y.¹ Virkar, A.A.² Mannsfeld, S.³ Oh, J.H.⁴ Toney, M.⁵ Locklin, A.⁶ Bao, Z.⁷

47
- 77949534444
- A. Amassian V. A. Pozdin R. Li M. D-Smilgies G. G. Malliaras J. Mater. Chem. 2010 20 2623 2629
- (2010) J. Mater. Chem. , vol.20 , pp. 2623-2629
- Amassian, A.¹ Pozdin, V.A.² Li, R.³ D-Smilgies, M.⁴ Malliaras, G.G.⁵

48
- 33745863908
- For reviews on chemical sensors based on organic thin film transistors, see
- K. C. Dickey J. E. Anthony Y.-L. Loo Adv. Mater 2006 18 1721 1726
- (2006) Adv. Mater , vol.18 , pp. 1721-1726
- Dickey, K.C.¹ Anthony, J.E.² Loo, Y.-L.³

49
- 65949106392
- M. E. Roberts A. N. Sokolov Z. Bao J. Mater. Chem. 2009 19 3351 3363
- (2009) J. Mater. Chem. , vol.19 , pp. 3351-3363
- Roberts, M.E.¹ Sokolov, A.N.² Bao, Z.³

50
- 77956971211
- T. Someya A. Dodabalapur J. Huang K. C. See H. Katz Adv. Mater. 2010 22 3799 3811
- (2010) Adv. Mater. , vol.22 , pp. 3799-3811
- Someya, T.¹ Dodabalapur, A.² Huang, J.³ See, K.C.⁴ Katz, H.⁵

51
- 29544444088
- J. T. Mabeck G. G. Malliaras Anal. Bioanal. Chem. 2006 384 343 353
- (2006) Anal. Bioanal. Chem. , vol.384 , pp. 343-353
- Mabeck, J.T.¹ Malliaras, G.G.²

52
- 29544448073
- J. Locklin Z. Bao Anal. Bioanal. Chem. 2006 384 336 342
- (2006) Anal. Bioanal. Chem. , vol.384 , pp. 336-342
- Locklin, J.¹ Bao, Z.²

53
- 29544438005
- L. Wang D. Fine D. Sharma L. Torsi A. Dodabalapur Anal. Bioanal. Chem. 2006 384 310 321
- (2006) Anal. Bioanal. Chem. , vol.384 , pp. 310-321
- Wang, L.¹ Fine, D.² Sharma, D.³ Torsi, L.⁴ Dodabalapur, A.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.