Issue
Korean Journal of Chemical Engineering,
Vol.38, No.7, 1308-1316, 2021
Radical-driven photocatalytic transformation of organic molecules
In photocatalysis, photons are absorbed by semiconductor materials and photogenerated electrons and holes migrate to the catalytic surface for desired reactions. Photocatalytic reduction and oxidation of organic molecules pose significant challenges and opportunities, with the surging demand for energy-efficient and carbon-neutral organic synthesis. In this review, we highlight the recent progress in the expanding area of radical-driven photocatalytic transformation of organic molecules. Our focus expands from heterogeneous catalysts to quantum dots, summarizing the reaction mechanism and photocatalytic activity, in reference to conventional molecular catalysts.
[References]
  1. Fujishima HKA, Nature, 238, 38, 1972
  2. Esswein MJ, Nocera DG, Chem. Rev., 107(10), 4022, 2007
  3. Kudo A, Miseki Y, Chem. Soc. Rev., 38, 253, 2009
  4. Holladay JD, Hu J, King DL, Wang Y, Catal. Today, 139, 244, 2009
  5. Maeda K, Domen K, J. Phys. Chem. Lett., 1, 2655, 2010
  6. Kim WD, Kim JH, Lee S, Lee S, Woo JY, Lee K, Chae WS, et al., Chem. Mater., 28, 962, 2016
  7. Lee KH, Lee CH, Cheong JY, Lee SK, Kim ID, Joh HI, Lee DC, Korean J. Chem. Eng., 34(12), 3214, 2017
  8. Chen S, Takata T, Domen K, Nat. Rev. Mater., 2, 1, 2017
  9. Takata T, Jiang JZ, Sakata Y, Nakabayashi M, Shibata N, Nandal V, Seki K, Hisatomi T, Domen K, Nature, 581(7809), 411, 2020
  10. Yu JG, Low JX, Xiao W, Zhou P, Jaroniec M, J. Am. Chem. Soc., 136(25), 8839, 2014
  11. Wang K, Li Q, Liu B, Cheng B, Ho W, Yu J, Appl. Catal. B: Environ., 176-177, 44, 2015
  12. Cho H, Kim WD, Lee K, Lee S, Kang GS, Joh HL, Lee DC, Appl. Surf. Sci., 429, 2, 2018
  13. Cho H, Kim WD, Yu J, Lee S, Lee DC, ChemCatChem, 10, 5679, 2018
  14. Jeong S, Kim GM, Kang GS, Kim C, Lee H, Kim WJ, Lee YK, Lee S, Kim H, Lim HK, Lee DC, J. Phys. Chem. C, 123, 29184, 2019
  15. Li D, Haneda H, Hishita S, Ohashi N, Chem. Mater., 17, 2596, 2005
  16. Mo J, Zhang Y, Xu Q, Lamson JJ, Zhao R, Atmos. Environ., 43, 2229, 2009
  17. Ochiai T, Fujishima A, J. Photochem. Photobiol. C Photochem. Rev., 13, 247, 2012
  18. Ghosh I, Marzo L, Das A, Shaikh R, Konig B, Accounts Chem. Res., 49, 1566, 2016
  19. Lin SS, Ischay MA, Fry CG, Yoon TP, J. Am. Chem. Soc., 133(48), 19350, 2011
  20. Cismesia MA, Yoon TP, Chem. Sci., 6, 5426, 2015
  21. Ahmed SN, Haider W, Nanotechnology, 29, 342001, 2018
  22. Huang C, Wen J, Shen Y, He F, Mi L, Gan Z, Ma J, Liu S, Ma H, Zhang Y, Chem. Sci., 9, 7912, 2018
  23. Adachi T, Latthe SS, Gosavi SW, Roy N, Suzuki N, Ikari H, Kato K, Katsumata K, Nakata K, Furudate M, Inoue T, Kondo T, Yuasa M, Fujishima A, Terashima C, Appl. Surf. Sci., 458, 917, 2018
  24. Zhang J, Chen X, Takanabe K, Maeda K, Domen K, Epping JD, Fu X, Antonieta M, Wang X, Angew. Chem.-Int. Edit., 49, 441, 2010
  25. Zhu J, Xiao P, Li H, Carabineiro SAC, ACS Appl. Mater. Interfaces, 6, 16449, 2014
  26. Zhang ZY, Edme K, Lian S, Weiss EA, J. Am. Chem. Soc., 139(12), 4246, 2017
  27. Caputo JA, Frenette LC, Zhao N, Sowers KL, Krauss TD, Weix DJ, J. Am. Chem. Soc., 139(12), 4250, 2017
  28. Caruge JM, Halpert JE, Wood V, Bulovi V, Bawendi MG, Nat. Photonics., 2, 247, 2008
  29. Wood V, Bulovic V, Nano Rev., 1, 5202, 2010
  30. Xu YF, Yang MZ, Chen BX, Wang XD, Chen HY, Kuang DB, Su CY, J. Am. Chem. Soc., 139(16), 5660, 2017
  31. Ge L, Zuo F, Liu J, Ma Q, Wang C, Sun D, Bartels L, Feng P, J. Phys. Chem. C, 116, 13708, 2012
  32. Rabouw FT, de Mello Donega C, Top. Curr. Chem., 374, 2016
  33. Lee H, Yoon DE, Koh S, Kang MS, Lim J, Lee DC, Chem. Sci., 11, 2318, 2020
  34. Kim D, Lee DC, J. Phys. Chem. Lett., 11, 2647, 2020
  35. Liu H, Li H, Lu J, Zeng S, Wang M, Luo N, Xu S, Wang F, ACS Catal., 8, 4761, 2018
  36. Wu X, Fang X, Xie S, Lin J, Cheng J, Zhang Q, Chen L, Wang Y, Nat. Catal., 1, 772, 2018
  37. Yin LX, Liebscher J, Chem. Rev., 107(1), 133, 2007
  38. Yeung CS, Dong VM, Chem. Rev., 111(3), 1215, 2011
  39. Miyaura N, Yamada K, Suzuki A, Tetrahedron Lett., 20, 3437, 1979
  40. Zoller J, Fabry CD, Rueping M, ACS Catal., 5, 3900, 2015
  41. Zhao Y, Antonietti M, Angew. Chem.-Int. Edit., 129, 9464, 2017
  42. McClelland KP, Clemons TD, Stupp SI, Weiss EA, ACS Macro Lett., 9, 7, 2020
  43. Kuriechen SK, Murugesan S, Raj SP, J. Catal., 2013, 1, 2013
  44. Hirakawa T, Yawata K, Nosaka Y, Appl. Catal. A: Gen., 325(1), 105, 2007
  45. Konstantinou IK, Albanis TA, Appl. Catal. B: Environ., 49(1), 1, 2004
  46. Auffan M, Pedeutour M, Rose J, Masion A, Ziarelli F, et al., Environ. Sci. Technol., 44, 2689, 2010
  47. Li Y, Tang L, Peng S, Li Z, Lu G, CrystEngComm, 14, 6974, 2012
  48. Park H, Ou HH, Kang U, Choi J, Hoffmann MR, Catal. Today, 266, 153, 2016
  49. Mitkina T, Stanglmair C, Setzer W, Gruber M, Kisch H, Konig B, Org. Biomol. Chem., 10, 3556, 2012
  50. Jensen SC, Homan SB, Weiss EA, J. Am. Chem. Soc., 138(5), 1591, 2016
  51. Lian S, Christensen JA, Kodaimati MS, Rogers CR, Wasielewski MR, Weiss EA, J. Phys. Chem. C, 123, 5923, 2019
  52. Thanh TH, Thanh DH, Lam VQ, Adv. Optoelectron., 2014, 9, 2014
  53. Cheng L, Xiang Q, Liao Y, Zhang H, Energy Environ. Sci., 11, 1362, 2018
  54. Noble A, MacMillan DWC, J. Am. Chem. Soc., 136(33), 11602, 2014
  55. Kim D, Lee YK, Lee D, Kim WD, Bae WK, Lee DC, ACS Nano, 11, 12461, 2017
  56. Yoon DE, Kim WD, Kim D, Lee D, Koh S, Bae WK, Lee DC, J. Phys. Chem. C, 121, 24837, 2017
  57. Kim WD, Yoon DE, Kim D, Koh S, Bae WK, Chae WS, Lee DC, J. Phys. Chem. C, 123, 9445, 2019
  58. Harris C, Kamat PV, ACS Nano, 4, 7321, 2010
  59. Ma C, Wu D, Yao X, Liu X, Wei M, Liu Y, Ma Z, Huo P, Yan Y, J. Alloy. Compd., 712, 486, 2017
  60. Xia W, Wu J, Hu JC, Sun S, Li MD, Liu H, Lan M, Wang F, ChemSusChem, 12, 4617, 2019
  61. Chakraborty IN, Roy S, Devatha G, Rao A, Pillai PP, Chem. Mater., 31, 2258, 2019
  62. Koh S, Eom T, Kim WD, Lee K, Lee D, Lee YK, Kim H, Bae WK, Lee DC, Chem. Mater., 29, 6346, 2017
  63. Lee DK, Koh SJ, Yoon DE, Lee SH, Kim WD,Kim DI, Bae WK, Lim JH, Lee DC, Korean J. Chem. Eng., 36(9), 1518, 2019
  64. Koh S, Lee H, Lee T, Park K, Kim WJ, Lee DC, J. Chem. Phys., 151, 144704, 2019
  65. Kim WD, Kim D, Yoon DE, Lee H, Lim J, Bae WK, Lee DC, Chem. Mater., 31, 3066, 2019
  66. Li L, Reiss P, J. Am. Chem. Soc., 130(35), 11588, 2008
  67. Martin JG, Hill RK, Chem. Rev., 61, 537, 1961
  68. Jiang X, Wang R, Chem. Rev., 113, 5515, 2013
  69. Guo Y, Chen T, Liu Q, Zhang Z, Fang X, J. Phys. Chem. C, 120, 25328, 2016
  70. Zhagn G, Lan ZA, Lin L, Lin S, Wang X, Chem. Sci., 7, 3062, 2016
  71. Wang X, Blechert S, Antonietti M, ACS Catal., 2, 1596, 2012
  72. Kang YY, Yang YQ, Yin LC, Kang XD, Liu G, Cheng HM, Adv. Mater., 27(31), 4572, 2015
  73. Zhu J, Xiao P, Li H, Carabineiro SAC, ACS Appl. Mater. Interfaces, 6, 16449, 2014
  74. Hu S, Li F, Fan Z, Wang F, Zhao Y, Lv Z, Dalt. Trans., 44, 1084, 2014
  75. Jones LO, Mosquera MA, Jiang Y, Weiss EA, Schatz GC, Ratner MA, J. Am. Chem. Soc., 142, 15488, 2020
  76. Nakayama K, Maeta N, Horiguchi G, Kamiya H, Okada Y, Org. Lett., 21, 2246, 2019
  77. Huang Y, Zhu Y, Egap E, ACS Macro Lett., 7, 184, 2018
  78. Jiao X, Zheng K, Chen Q, Li X, Li Y, Shao W, Xu J, Zhu J, Pan Y, Sun Y, Xie Y, Angew. Chem.-Int. Edit., 59, 15497, 2020
  79. Han G, Yan T, Zhang W, Zhang YC, Lee DY, Cao Z, Sun Y, ACS Catal., 9, 11341, 2019
  80. Gao Y, Zhang J, Chen X, Ma D, Yan N, Chempluschem, 79, 825, 2014
  81. Tsai YT, Chen CY, Hsieh YJ, Tsai ML, Eur. J. Inorg. Chem., 2019, 4637, 2019
  82. Gazi S, Ng WKH, Ganguly R, Moeljadi AMP, Hirao H, Soo HS, Chem. Sci., 6, 7130, 2015
  83. Enright MJ, Gilbert-Bass K, Sarsito H, Cossairt BM, Chem. Mater., 31, 2677, 2019
  84. Mu W, Herrmann JM, Pichat P, Catal. Lett., 3, 73, 1989
  85. Almquist CB, Biswas P, Appl. Catal. A: Gen., 214(2), 259, 2001
  86. Fujihira M, Satoh Y, Osa T, Nature, 293, 206, 1981
  87. Ohno T, Tokieda K, Higashida S, Matsumura M, Appl. Catal. A: Gen., 244(2), 383, 2003
  88. Yoshida H, Yuzawa H, Aoki M, Otake K, Itoh H, Hattori T, Chem. Commun., 4634 (2008).
  89. Wakerley DW, Kuehnel MF, Orchard KL, Ly KH, Rosser TE, Reisner E, Nat. Energy, 2, 1, 2017
  90. Charton M, J. Am. Chem. Soc., 97, 3691, 1975
  91. Stefanidis D, Jencks WP, J. Am. Chem. Soc., 115, 6045, 1993
  92. Uekert T, Kuehnel MF, Wakerley DW, Reisner E, Energy Environ. Sci., 11, 2853, 2018
  93. Uekert T, Kasap H, Reisner E, J. Am. Chem. Soc., 141(38), 15201, 2019
  94. Uekert T, Dorchies F, Pichler CM, Reisner E, Green Chem., 22, 3262, 2020
  95. Achilleos DS, Yang W, Kasap H, Savateev A, Markushyna Y, Durrant JR, Reisner E, Angew. Chem.-Int. Edit., 59, 18184, 2020
  96. Pichler CM, Uekert T, Reisner E, Chem. Commun., 56, 5743, 2020
  97. Okada Y, Maeta N, Nakayama K, Kamiya H, J. Org. Chem., 83, 4948, 2018