메뉴 건너뛰기




Volumn 14, Issue 27, 2008, Pages 8102-8115

Comparative study on the structural, optical, and electrochemical properties of bithiophene-fused benzo[c]phospholes

Author keywords

Conjugation; Fused ring systems; Phosphole; pi interactions; Thiophene

Indexed keywords

CONJUGATION; FUSED-RING SYSTEMS; PHOSPHOLE; PI INTERACTIONS; THIOPHENE;

EID: 53949101577     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801017     Document Type: Article
Times cited : (76)

References (92)
  • 2
    • 0347604144 scopus 로고
    • b) F. Mathey, Chem. Rev. 1988, 88, 429-453;
    • (1988) Chem. Rev , vol.88 , pp. 429-453
    • Mathey, F.1
  • 3
    • 0003607021 scopus 로고    scopus 로고
    • Eds, A. R. Kalritzky, C. W. Rees, E. F. V. Scriven, Elsevier, Oxford
    • c) L. D. Quin, in Comprehensive Heterocyclic Chemistry, Vol. 2 (Eds.: A. R. Kalritzky, C. W. Rees, E. F. V. Scriven), Elsevier, Oxford, 1996;
    • (1996) Comprehensive Heterocyclic Chemistry , vol.2
    • Quin, L.D.1
  • 5
    • 0035353483 scopus 로고    scopus 로고
    • e) L. Nyulászi, Chem. Rev. 2001, 101, 1229-1246;
    • (2001) Chem. Rev , vol.101 , pp. 1229-1246
    • Nyulászi, L.1
  • 6
    • 0141463985 scopus 로고    scopus 로고
    • f) F. Mathey, Angew. Chem. 2003, 115, 1616-1643;
    • (2003) Angew. Chem , vol.115 , pp. 1616-1643
    • Mathey, F.1
  • 7
    • 0037432895 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1578-1604;
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1578-1604
  • 10
    • 33947281309 scopus 로고    scopus 로고
    • T. Baumgartner, R. Réau, Chem. Rev. 2006, 106, 4681-4727 (corrigendum: T. Baumgartner. R. Réau, Chem. Rev. 2007, 107, 303):
    • b) T. Baumgartner, R. Réau, Chem. Rev. 2006, 106, 4681-4727 (corrigendum: T. Baumgartner. R. Réau, Chem. Rev. 2007, 107, 303):
  • 11
    • 76349121200 scopus 로고    scopus 로고
    • Eds, T.J.J. Müller, U. H. F. Bunz, Wiley-VCH. Weinheim
    • c) P. W. Dyer. R. Réau, in Functional Organic Materials (Eds.: T.J.J. Müller, U. H. F. Bunz), Wiley-VCH. Weinheim, 2007, pp. 119-177;
    • (2007) Functional Organic Materials , pp. 119-177
    • Dyer, P.W.1    Réau, R.2
  • 16
    • 0034657477 scopus 로고    scopus 로고
    • Angew. Chem. Im. Ed. 2000, 39, 1812-1815;
    • (2000) Angew. Chem. Im. Ed , vol.39 , pp. 1812-1815
  • 20
    • 33645416992 scopus 로고    scopus 로고
    • B. Nohra, S. Graule, C. Lescop, R. Réau, J. Am. Chem. Soc. 2006, 128, 3520-3521: see also references [2a-d].
    • f) B. Nohra, S. Graule, C. Lescop, R. Réau, J. Am. Chem. Soc. 2006, 128, 3520-3521: see also references [2a-d].
  • 36
    • 53949083928 scopus 로고    scopus 로고
    • S. Kobayashi, M. Noguchi, Y. Tsubata, M. Kitano, H. Doi, T. Kamioka, A. Nakazono, Jpn. Pal. 2003231741. 2003;
    • a) S. Kobayashi, M. Noguchi, Y. Tsubata, M. Kitano, H. Doi, T. Kamioka, A. Nakazono, Jpn. Pal. 2003231741. 2003;
  • 37
    • 2042441744 scopus 로고    scopus 로고
    • Y. Makioka, T. Hayashi, M. Tanaka. Chem. Lett. 2004, 33, 44-45; see also reference [4b].
    • b) Y. Makioka, T. Hayashi, M. Tanaka. Chem. Lett. 2004, 33, 44-45; see also reference [4b].
  • 40
    • 10044284169 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 6197-6201;
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 6197-6201
  • 46
    • 34547927179 scopus 로고    scopus 로고
    • The calculated dibenzo[è,d]phospholes bear phenyl or methyl group at the phosphorus center. In this study, we determined the HOMO and LUMO energies of unsubstituted dibenzo[b,d]phosphole at the B3LYP/6-31G» level as -6.00 and -1.00 eV, respectively
    • R.-F. Chen, C. Zheng, Q.-L. Fan, W. Huang, J. Comput. Chem. 2007, 28, 2091-2101. The calculated dibenzo[è,d]phospholes bear phenyl or methyl group at the phosphorus center. In this study, we determined the HOMO and LUMO energies of unsubstituted dibenzo[b,d]phosphole at the B3LYP/6-31G» level as -6.00 and -1.00 eV, respectively.
    • (2007) J. Comput. Chem , vol.28 , pp. 2091-2101
    • Chen, R.-F.1    Zheng, C.2    Fan, Q.-L.3    Huang, W.4
  • 52
    • 38349106934 scopus 로고    scopus 로고
    • Eds, D. Bellus, S.V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost, Thieme, New York
    • f) R. A. Aitken, in Science of Synthesis, Vol. 10 (Eds.: D. Bellus, S.V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost), Thieme, New York, 2000, pp. 809-815.
    • (2000) Science of Synthesis , vol.10 , pp. 809-815
    • Aitken, R.A.1
  • 53
    • 53949122570 scopus 로고    scopus 로고
    • A benzo[c]phosphole bearing triphenylphosphonio groups at the 2.5-positions was isolated as a highly moisture-sensitive solid, although its fundamental properties have not been reported. See: A. Schmidpeter, M. Thiele, Angew. Chem. 1991, 103, 333-335;
    • A benzo[c]phosphole bearing triphenylphosphonio groups at the 2.5-positions was isolated as a highly moisture-sensitive solid, although its fundamental properties have not been reported. See: A. Schmidpeter, M. Thiele, Angew. Chem. 1991, 103, 333-335;
  • 55
    • 38349180146 scopus 로고    scopus 로고
    • Preliminary results were reported as a Communication. See
    • Preliminary results were reported as a Communication. See: T. Miyajima, Y. Matano, H. Imahori, Eur. J. Org. Chem. 2008, 255-259.
    • (2008) Eur. J. Org. Chem , pp. 255-259
    • Miyajima, T.1    Matano, Y.2    Imahori, H.3
  • 56
    • 33746376111 scopus 로고    scopus 로고
    • For the syntheses of phospholes via titanacyclopentadienes, see: a
    • For the syntheses of phospholes via titanacyclopentadienes, see: a) I. Tomita, Polym. Prepr. 2004, 45, 415-416;
    • (2004) Polym. Prepr , vol.45 , pp. 415-416
    • Tomita, I.1
  • 57
    • 33746338281 scopus 로고    scopus 로고
    • Y. Matano. T. Miyajima. T. Nakabuchi, Y. Matsutani. H. Imahori, J. Org. Chem. 2006, 71, 5792-5795: see also references [5d,e], [6b], and [15].
    • b) Y. Matano. T. Miyajima. T. Nakabuchi, Y. Matsutani. H. Imahori, J. Org. Chem. 2006, 71, 5792-5795: see also references [5d,e], [6b], and [15].
  • 62
    • 53949098869 scopus 로고    scopus 로고
    • Eds, D. Bellus, S. V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost, Thieme, New York, and references therein
    • d) K. Mikami, Y. Matsumolo, T. Shiono, in Science of Synthesis, Vol. 2 (Eds.: D. Bellus, S. V. Ley, R. Noyori, M. Regitz, P. J. Reider, E. Schaumann, I. Shinkai, E. J. Thomas, B. M. Trost). Thieme, New York, 2003, pp. 809-815, and references therein.
    • (2003) Science of Synthesis , vol.2 , pp. 809-815
    • Mikami, K.1    Matsumolo, Y.2    Shiono, T.3
  • 63
    • 53949100146 scopus 로고    scopus 로고
    • In single crystals of 8a and 9a, one dichloromethane molecule was incorporated per two benzo[c]phosphole molecules, whose structures are very similar. Therefore, the data for one of the pair are listed for 8a and 9a in Table 1.
    • In single crystals of 8a and 9a, one dichloromethane molecule was incorporated per two benzo[c]phosphole molecules, whose structures are very similar. Therefore, the data for one of the pair are listed for 8a and 9a in Table 1.
  • 64
    • 0000592485 scopus 로고    scopus 로고
    • S. Attar, W. H. Bearden, N. W. Alcock, E. C. Alyea, J. H. Nelson, lnorg. Chem. 1990, 29, 425-433; Au-P, 2.220(9)-2.227(2) Å P-AuCl, 172.4(1)-178.8(1)°
    • a) S. Attar, W. H. Bearden, N. W. Alcock, E. C. Alyea, J. H. Nelson, lnorg. Chem. 1990, 29, 425-433; Au-P, 2.220(9)-2.227(2) Å P-AuCl, 172.4(1)-178.8(1)°
  • 65
    • 53949090921 scopus 로고    scopus 로고
    • See refernce [4b]; Au-P, 2.2290(16)2.2300(16) Å P-Au-Cl, 171.64(7)-174.63(8)°;
    • b) See refernce [4b]; Au-P, 2.2290(16)2.2300(16) Å P-Au-Cl, 171.64(7)-174.63(8)°;
  • 66
    • 53949117880 scopus 로고    scopus 로고
    • Y. Dienes. M. Eggenstein, T. Neumann, U. Englert, T. Baumgartner, Dalton Trans. 2006, 1424-1433; Au-P, 2.2249(12) Å P-Au-Cl. 177.26(4)°: Au-P, 2.228(2) Å P-Au-Cl, 177.26(4)°;
    • c) Y. Dienes. M. Eggenstein, T. Neumann, U. Englert, T. Baumgartner, Dalton Trans. 2006, 1424-1433; Au-P, 2.2249(12) Å P-Au-Cl. 177.26(4)°: Au-P, 2.228(2) Å P-Au-Cl, 177.26(4)°;
  • 67
    • 53949087499 scopus 로고    scopus 로고
    • see reference [9c]; Au-P, 2.228(2) Å P-Au-Cl, 175.59(7)°.
    • d)see reference [9c]; Au-P, 2.228(2) Å P-Au-Cl, 175.59(7)°.
  • 68
    • 53949096439 scopus 로고    scopus 로고
    • The π-π distances between two planes in 7a, 8a, and 9a are about 3.4-3.6 Å.
    • The π-π distances between two planes in 7a, 8a, and 9a are about 3.4-3.6 Å.
  • 69
    • 53949121266 scopus 로고    scopus 로고
    • The electronic factor, namely dipole-dipole interaction of the adjacent chromophores, may also assist the head-to-head orientation of 7a, 8a, and 9a
    • The electronic factor, namely dipole-dipole interaction of the adjacent chromophores, may also assist the head-to-head orientation of 7a, 8a, and 9a.
  • 71
    • 53949088158 scopus 로고    scopus 로고
    • The slower rise component was quenched by the addition of oxygen into the solution
    • The slower rise component was quenched by the addition of oxygen into the solution.
  • 72
    • 53949097702 scopus 로고    scopus 로고
    • In our preliminary communication, we reported the optimized structures of P-phenyl analogues of 4m-6m, whose HOMO and LUMO energies are as follows: 4m-Ph, 5.10 eV and -1.89 eV, 5m-Ph, 5.16 and -1.96 eV, 6m-Ph, 5.55 and -1.60 eV, See reference [15
    • In our preliminary communication, we reported the optimized structures of P-phenyl analogues of 4m-6m, whose HOMO and LUMO energies are as follows: 4m-Ph (-5.10 eV and -1.89 eV), 5m-Ph (-5.16 and -1.96 eV). 6m-Ph (-5.55 and -1.60 eV). See reference [15].
  • 73
    • 33646501562 scopus 로고    scopus 로고
    • There are some reports on OLEDs using triorganylphosphine oxides as the component of electron transporting layers. For example, see: a P. E. Burrows, A.B. Padmaperuma, L. S. Sapochak, P. Djurovich, M. E. Thompson, Appl. Phys. Lett. 2006, 88, 183503;
    • There are some reports on OLEDs using triorganylphosphine oxides as the component of electron transporting layers. For example, see: a) P. E. Burrows, A.B. Padmaperuma, L. S. Sapochak, P. Djurovich, M. E. Thompson, Appl. Phys. Lett. 2006, 88, 183503;
  • 78
    • 53949095985 scopus 로고    scopus 로고
    • The negative field dependency of the mobility has been observed for several hole/eleclron-transporting materials. For example, see: Organic Photoreceptors for Xerography P. M. Borsenberger, D. S. Weiss, Optical Engineering 59 Ed, B.J. Thompson, Marcel Dekker. New York, 1998, pp. 300-305
    • The negative field dependency of the mobility has been observed for several hole/eleclron-transporting materials. For example, see: "Organic Photoreceptors for Xerography" P. M. Borsenberger, D. S. Weiss, Optical Engineering Vol. 59 (Ed.: B.J. Thompson), Marcel Dekker. New York, 1998, pp. 300-305.
  • 79
    • 0000858855 scopus 로고    scopus 로고
    • 3 reported by Naka and co-workers are about 2.5 times larger than our experimental values. See: a S. Naka, H. Okada, H. Onnagawa, T. Tsutsui, Appl. Phys. Lett. 2000, 76, 197-199;
    • 3 reported by Naka and co-workers are about 2.5 times larger than our experimental values. See: a) S. Naka, H. Okada, H. Onnagawa, T. Tsutsui, Appl. Phys. Lett. 2000, 76, 197-199;
  • 81
    • 52649112790 scopus 로고    scopus 로고
    • During the preparation of our manuscript, Tsuji, Nakamura. and coworkers reported the electron mobility of a benzo[b]phosphole oxide by the TOF technique using a vacuum-deposited film. See: H. Tsuji, K. Sato, L. Hies, Y. Itoh, Y. Sato, E. Nakamura. Org. Lett. 2008, 10, 2263-2265.
    • During the preparation of our manuscript, Tsuji, Nakamura. and coworkers reported the electron mobility of a benzo[b]phosphole oxide by the TOF technique using a vacuum-deposited film. See: H. Tsuji, K. Sato, L. Hies, Y. Itoh, Y. Sato, E. Nakamura. Org. Lett. 2008, 10, 2263-2265.
  • 84
    • 53949105145 scopus 로고    scopus 로고
    • DIRDIF99: Beurskens, P. T., Admiraal, G., Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen (The Netherlands), 1999.
    • DIRDIF99: Beurskens, P. T., Admiraal, G., Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen (The Netherlands), 1999.
  • 85
    • 53949105593 scopus 로고    scopus 로고
    • CrystalStructure 3.8.0: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC (2000-2006). 9009 New Trails Dr. The Woodlands, TX 77381, USA.
    • CrystalStructure 3.8.0: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC (2000-2006). 9009 New Trails Dr. The Woodlands, TX 77381, USA.
  • 86
    • 0004150157 scopus 로고    scopus 로고
    • University of Götlingen Germany
    • G. M. Sheldrick, SHELXL-97, University of Götlingen (Germany). 1997.
    • (1997) SHELXL-97
    • Sheldrick, G.M.1
  • 87
    • 53949103455 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery,Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Slratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, O. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery,Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Slratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, O. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03. Gaussian, Pittsburgh, PA, 2003.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.