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Mechanistic investigation by using tailored competition experiments and kinetic simulation provides a comprehensive model, supporting a chain\u2010growth mechanism underlying the one\u2010pot formation of aromatic pentamers, whereby the successive addition of a bifunctional monomer unit onto either another monomer or the growing oligomeric backbone is faster than other types of bimolecular condensations involving oligomers longer than monomers. DFT calculations at the B3LYP\/6\u201031G* level reveal the five\u2010residue pentamer to be the most stable with respect to alternative four\u2010, six\u2010, and seven\u2010residue macrocycles. These novel mechanistic insights may become useful in analyzing other macrocyclization, oligomerization, and ploymerization reactions.<\/jats:p>","DOI":"10.1002\/asia.201100409","type":"journal-article","created":{"date-parts":[[2011,7,20]],"date-time":"2011-07-20T09:44:33Z","timestamp":1311155073000},"page":"3298-3305","source":"Crossref","is-referenced-by-count":22,"title":["One\u2010Pot Multimolecular Macrocyclization for the Expedient Synthesis of Macrocyclic Aromatic Pentamers by a Chain Growth Mechanism"],"prefix":"10.1002","volume":"6","author":[{"given":"Bo","family":"Qin","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sheng","family":"Shen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chang","family":"Sun","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiyun","family":"Du","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kun","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huaqiang","family":"Zeng","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2011,7,20]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00986a052"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01002a035"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)88299-X"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)88300-3"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00789a050"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00790a052"},{"key":"e_1_2_6_7_2","unstructured":"\u00a0"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1007\/3-540-54348-1_6"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19981016)110:20<2985::AID-ANGE2985>3.0.CO;2-4"},{"key":"e_1_2_6_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19981102)37:20<2825::AID-ANIE2825>3.0.CO;2-Y"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200305496"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200503988"},{"key":"e_1_2_6_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503988"},{"key":"e_1_2_6_12_2","unstructured":"\u00a0"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00401a050"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19881000106"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198800051"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/b510118b"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2005.11.082"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/b704366j"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol801083r"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802801n"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.02.186"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/b503921e"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0602912103"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol8028884"},{"key":"e_1_2_6_24_2","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39940001277"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0474547"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0526322"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.2008.10"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja807935y"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0488643"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/b603985e"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200900584"},{"key":"e_1_2_6_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200900584"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527209787193765"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.02.207"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc05791f"},{"key":"e_1_2_6_36_2","unstructured":"B. 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