Reaction SMILES: [C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:49]3[C:16](=[CH:17][C:18]4[C:19](=[O:119])[C:20]5[C:45]([C:46](=[O:50])[C:47]=4[CH:48]=3)=[CH:44][C:43]3[C:22](=[C:23]([S:108][C:109]4[CH:114]=[CH:113][C:112]([C:115]([CH3:118])([CH3:117])[CH3:116])=[CH:111][CH:110]=4)[C:24]4[C:41]([C:42]=3[S:51][C:52]3[CH:57]=[CH:56][C:55]([C:58]([CH3:61])([CH3:60])[CH3:59])=[CH:54][CH:53]=3)=[CH:40][C:39]3[C:38](=[O:62])[C:37]6[C:28](=[CH:29][C:30]7[C:35]([CH:36]=6)=[C:34]([S:63][C:64]6[CH:69]=[CH:68][C:67]([C:70]([CH3:73])([CH3:72])[CH3:71])=[CH:66][CH:65]=6)[C:33]([S:74][C:75]6[CH:80]=[CH:79][C:78]([C:81]([CH3:84])([CH3:83])[CH3:82])=[CH:77][CH:76]=6)=[C:32]([S:85][C:86]6[CH:91]=[CH:90][C:89]([C:92]([CH3:95])([CH3:94])[CH3:93])=[CH:88][CH:87]=6)[C:31]=7[S:96][C:97]6[CH:102]=[CH:101][C:100]([C:103]([CH3:106])([CH3:105])[CH3:104])=[CH:99][CH:98]=6)[C:27](=[O:107])[C:26]=3[CH:25]=4)[CH:21]=5)[C:15]([S:120][C:121]3[CH:126]=[CH:125][C:124]([C:127]([CH3:130])([CH3:129])[CH3:128])=[CH:123][CH:122]=3)=[C:14]([S:131][C:132]3[CH:137]=[CH:136][C:135]([C:138]([CH3:141])([CH3:140])[CH3:139])=[CH:134][CH:133]=3)[C:13]=2[S:142][C:143]2[CH:148]=[CH:147][C:146]([C:149]([CH3:152])([CH3:151])[CH3:150])=[CH:145][CH:144]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[C:49]3[C:16](=[CH:17][C:18]4[CH:19]([OH:119])[C:20]5[C:45]([CH:46]([OH:50])[C:47]=4[CH:48]=3)=[CH:44][C:43]3[C:22](=[C:23]([S:108][C:109]4[CH:110]=[CH:111][C:112]([C:115]([CH3:116])([CH3:117])[CH3:118])=[CH:113][CH:114]=4)[C:24]4[C:41]([C:42]=3[S:51][C:52]3[CH:53]=[CH:54][C:55]([C:58]([CH3:59])([CH3:60])[CH3:61])=[CH:56][CH:57]=3)=[CH:40][C:39]3[CH:38]([OH:62])[C:37]6[C:28](=[CH:29][C:30]7[C:35]([CH:36]=6)=[C:34]([S:63][C:64]6[CH:65]=[CH:66][C:67]([C:70]([CH3:71])([CH3:72])[CH3:73])=[CH:68][CH:69]=6)[C:33]([S:74][C:75]6[CH:80]=[CH:79][C:78]([C:81]([CH3:82])([CH3:83])[CH3:84])=[CH:77][CH:76]=6)=[C:32]([S:85][C:86]6[CH:91]=[CH:90][C:89]([C:92]([CH3:95])([CH3:94])[CH3:93])=[CH:88][CH:87]=6)[C:31]=7[S:96][C:97]6[CH:102]=[CH:101][C:100]([C:103]([CH3:106])([CH3:105])[CH3:104])=[CH:99][CH:98]=6)[CH:27]([OH:107])[C:26]=3[CH:25]=4)[CH:21]=5)[C:15]([S:120][C:121]3[CH:122]=[CH:123][C:124]([C:127]([CH3:130])([CH3:129])[CH3:128])=[CH:125][CH:126]=3)=[C:14]([S:131][C:132]3[CH:137]=[CH:136][C:135]([C:138]([CH3:141])([CH3:140])[CH3:139])=[CH:134][CH:133]=3)[C:13]=2[S:142][C:143]2[CH:148]=[CH:147][C:146]([C:149]([CH3:152])([CH3:151])[CH3:150])=[CH:145][CH:144]=2)=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]
Reactant: CC(C)(C)c1ccc(Sc2c(Sc3ccc(C(C)(C)C)cc3)c(Sc3ccc(C(C)(C)C)cc3)c3cc4c(=O)c5cc6c(Sc7ccc(C(C)(C)C)cc7)c7cc8c(=O)c9cc%10c(Sc%11ccc(C(C)(C)C)cc%11)c(Sc%11ccc(C(C)(C)C)cc%11)c(Sc%11ccc(C(C)(C)C)cc%11)c(Sc%11ccc(C(C)(C)C)cc%11)c%10cc9c(=O)c8cc7c(Sc7ccc(C(C)(C)C)cc7)c6cc5c(=O)c4cc3c2Sc2ccc(C(C)(C)C)cc2)cc1
Agent: [BH4-]
Agent: [Na+]
Solvent: C1CCOC1
Product: CC(C)(C)c1ccc(Sc2c(Sc3ccc(C(C)(C)C)cc3)c(Sc3ccc(C(C)(C)C)cc3)c3cc4c(cc3c2Sc2ccc(C(C)(C)C)cc2)C(O)c2cc3c(Sc5ccc(C(C)(C)C)cc5)c5cc6c(cc5c(Sc5ccc(C(C)(C)C)cc5)c3cc2C4O)C(O)c2cc3c(Sc4ccc(C(C)(C)C)cc4)c(Sc4ccc(C(C)(C)C)cc4)c(Sc4ccc(C(C)(C)C)cc4)c(Sc4ccc(C(C)(C)C)cc4)c3cc2C6O)cc1
Temperature: 25 °C
Reaction time: 3 h
Yield: 93.3 %

Procedure:
To a suspension of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)nonacene-6,10,17,21-tetraone (0.5 g, 0.23 mmol) in dry THF (10 mL) under a N2 atmosphere was slowly added NaBH4 (0.1 g, 2.64 mmol). The reaction mixture was stirred at room temp for 3 h, and then quenched with H2O. The resulting mixture was filtered, washed with H2O, and dried in vacuo to give the desired product as a light yellow solid (0.47 g, 94%). LDI-MS m/z: 2188 [M+], 2171 [M+-OH]. The laser desorption ionization mass spectrum (LDI-MS) of 1,2,3,4,8,12,13,14,15,19-deca(4′-t-butylphenylthio)-6,10,17,21-tetrahydrononacene-6,10,17,21-tetraol is shown in FIG. 14B. The compound structure is shown in FIG. 14A.