34904-46-6Relevant articles and documents
Spiroconjugated Tetraaminospirenes as Donors in Color-Tunable Charge-Transfer Emitters with Donor-Acceptor Structure
Grenz, David C.,Rose, Daniel,W?ssner, Jan S.,Wilbuer, Jennifer,Adler, Florin,Hermann, Mathias,Chan, Chin-Yiu,Adachi, Chihaya,Esser, Birgit
supporting information, (2021/12/22)
Charge-transfer emitters are attractive due to their color tunability and potentially high photoluminescence quantum yields (PLQYs). We herein present tetraaminospirenes as donor moieties, which, in combination with a variety of acceptors, furnished 12 charge-transfer emitters with a range of emission colors and PLQYs of up to 99 %. The spatial separation of their frontier molecular orbitals was obtained through careful structural design, and two DA structures were confirmed by X-ray crystallography. A range of photophysical measurements supported by DFT calculations shed light on the optoelectronic properties of this new family of spiro-NN-donor-acceptor dyes.
Design, synthesis and biological evaluation of novel perimidine o-quinone derivatives as non-intercalative topoisomerase II catalytic inhibitors
Zhou, Du-Chao,Lu, Yu-Ting,Mai, Yan-Wen,Zhang, Chen,Xia, Jie,Yao, Pei-Fen,Wang, Hong-Gen,Huang, Shi-Liang,Huang, Zhi-Shu
, (2019/08/06)
For the development of novel anticancer agents, we designed and synthesized a total of 37 perimidine o-quinone derivatives containing the o-quinone group at the A or B ring and different substituents (alkyl groups, aryl groups or heterocycles) at the C ri
Perimidine quinone derivatives and preparation method and applications thereof
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Paragraph 0032; 0039; 0042, (2019/01/08)
The invention belongs to the technical fields of medicine and chemical engineering, and discloses Perimidine quinone derivatives and a preparation method and an application thereof on the preparationof antitumor drugs. The structural formula of related Pe
Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; Conformationally-controlled oligomers bearing electroactive groups
Alder, Roger W.,Hyland, Niall P.,Jeffery, John C.,Riis-Johannessen, Thomas,Riley, D. Jason
supporting information; experimental part, p. 2704 - 2715 (2009/09/07)
The design of polymers with repeating [C(NR2)2CH 2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2 groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH 2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed. The Royal Society of Chemistry 2009.
Optical properties of spiroconjugated charge-transfer dyes
Maslak, Przemyslaw,Chopra, Anu,Moylan, Christopher R.,Wortmann, Rüdiger,Lebus, Sonja,Rheingold, Arnold L.,Yap, Glenn P. A.
, p. 1471 - 1481 (2007/10/03)
A new type of intramolecular charge-transfer dye has been prepared. The LUMO of the acceptor part (1,3-indandione) in these compounds is spiroconjugated with the HOMO of the donor part (aromatic diamine or amino thiol). The interaction between the donor and acceptor is controlled by the energy and symmetry of the frontier orbitals. The ground state dipole moments of these compounds are aligned along the long molecular axes. In the solid state, distortions of structures are observed that are consistent with partial electron shift from the donor to the acceptor. Much more pronounced electron density shifts accompany the electronic transition that is observed in the visible region of the spectrum. These transitions are of the charge-transfer (CT) type, as shown by solvatochromic and electrooptical studies. The excited state dipole moments are in the direction opposite to that of the ground state. These observations are consistent with the excited state having radical ion pair character. The new dyes are modeled using a simple Mulliken charge-transfer theory. The mixing coefficient of neutral and ionic wave functions describing these systems is used as a measure of spiroconjugation between the subchromophores. The electrooptical data provide an estimate of the contribution of the CT transitions to the hyperpolarizabilities (β) within the two-state model. The measured values of β indicate, however, that spiro dyes have two opposing contributions to their hyperpolarizabilities, one from the CT transition and one due to the acceptor subchromophore.
PERI-NAPHTHYLENE DIAMINES III. CONVENIENT METHOD FOR THE ALKYLATION OF 1,8-NAPHTHYLENEDIAMINES AND PERIMIDINES
Kurasov, L. A.,Posharskii, A. F.,Kuz'menko, V. V.
, p. 1735 - 1738 (2007/10/02)
In dimethyl sulfoxide or hexamethylphosphorotriamide in the presence of potassium hydroxide 1,8-naphthylenediamine is readily alkylated by an excess of methyl and ethyl iodide to the corresponding 1,8-bis(dialkylamino)naphthalene.Perimidone, which has low basicity, is methylated to 1,3-dimethylperimidone under these conditions.The potassium hydroxide-dimethyl sulfoxide system also secures higher yields of the N-substituted products during the alkylation of perimidine, 2-methylperimidine, and aceperimidine by alkyl halides compared with the potassium hydroxide-alcoholsystem.The yield and structure of the products from benzylation of the perimidines depend on the presence of substituents at position 2 of the heterocyclic system of perimidine.
