• 专利标题:   Making substituted diazaperopyrenium dication used e.g. converting graphite to exfoliated graphene, comprises reacting substituted 1,3,8,10-tetrahydro-2,9-diazadibenzo(cd,lm)perylene with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
  • 专利号:   US2016368913-A1, US9828371-B2
  • 发明人:   STODDART J F, BASURAY A N, HARTLIEB K J, SAMPATH S, DE ROUVILLE H J
  • 专利权人:   UNIV NORTHWESTERN
  • 国际专利分类:   C01B031/04, C07D471/04
  • 专利详细信息:   US2016368913-A1 22 Dec 2016 C07D-471/04 201708 Pages: 30 English
  • 申请详细信息:   US2016368913-A1 US499074 26 Sep 2014
  • 优先权号:   US883352P, US499074

▎ 摘  要

NOVELTY - Making substituted diazaperopyrenium dication (II), comprises: providing substituted 1,3,8,10-tetrahydro-2,9-diazadibenzo(cd,lm)perylene (I); providing 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; and reacting (I) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form (II). (II) is neutrally-balanced with counterion(s) (Q-) including e.g. acetate, aceturate, acistrate, besylate and bromide. USE - The method is useful for making (II) which is useful: for converting graphite to exfoliated graphene (claimed) in water at room temperature; in organic solar cells, organic field effect transistors, organic dyes and fluorescent probes; in photocatalysts for water splitting and carbon dioxide reduction, iodine-doped semiconductors, singlet oxygen generator, chemotherapeutic agents (e.g. DNA intercalation and base-specific cleavage activities) and in waste water treatment. ADVANTAGE - This method is unique over the well-known Hummer's method of creating graphene. DETAILED DESCRIPTION - Making substituted diazaperopyrenium dication of formula (II), comprises: providing substituted 1,3,8,10-tetrahydro-2,9-diazadibenzo(cd,lm)perylene of formula (I); providing 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; and reacting (I) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form (II). (II) is neutrally-balanced with counterion(s) (Q-) including acetate, aceturate, acistrate, besylate, bromide, buciclate, butyrate, camsylate, caproate, citrate, chloride, closylate, cypionate, dapropate, edetate, edisylate, elaidate, enanthate, estolate, esylate, etabonate, etemesil, ethyl sulfate, etzadroxil, formate, fostedate, fumarate, furoate, hemisuccinate, hybenzate, hydroxide, iodide, isethionate, lactate, laurate, maleate, mebutate, mesylate, napadisylate, napsylate, nitrite, oleate, oxalate, palmitate, pamoate, phosphate, perchlorate, phenylpropionate, pivalate, propionate, salicylate, sesquioleate, stearate, succinate, sulfate, tartate, thiocyanate, tebutate, tosylate, triflate, trifluoroacetate, valerate, xinafoate, tetrafluoroborate or hexafluorophosphate. R1, R2 = phenyl substituted moiety of formula (a), heterocyclic moiety of formula (b), -C(R5)(R6), -(CH2)n-CH2-R7 or -CH2-(CH2-O-CH(R9))n-CH2-R8; R3-R8 = H, halo, 1-18C alkyl, 2-18C alkenyl, 2-18C alkynyl, 3-8C cycloalkyl, 3-8C heterocycloalkyl 5-20C aryl, 5-20C heteroaryl, alcohol, aldehyde, ester, carboxylic acid, anhydride, carboxamide, amine, hydroxylamine, oxime, azide, CN, ether, thiol, thioether, sulfoxide or sulfone; R9 = H and CH3; and n = 0-18. An INDEPENDENT CLAIM is also included for converting graphite to exfoliated graphene, comprising: providing graphite; providing (II); and mixing graphite with (II) to form exfoliated graphene.