摘要
合成了12个氨基联苯基苯并[de]异喹啉-1,3-二酮和苯并咪唑[2,1-a]苯并[de]异喹啉-7-酮类衍生物,其中2个手性化合物3b的[α]25579=-59°(c=0.2,DMF),化合物8b的[α]25579=-96°(c=0.1,THF);分离了2(5)-硝基和3(4)-氯代苯并咪唑苯并异喹啉-7-酮类异构体(化合物5a与6a、5b与6b)并提供了相关的波谱数据;同时探讨了芳环上的亲核取代(SN2Ar)反应机制。测定了所合成化合物的紫外吸收、荧光光谱,并计算了相对荧光效率(Φf)。结果显示,此类化合物的荧光效率、stokes位移以及摩尔吸光系数均受共轭程度与取代基的影响。
12 Benzisoquinolinone analogues were synthesized, which contained two chirality compounds with [α]579^25 = -59°（c =0. 2,DMF）（3b） and [α] 579^25 = -96°（c =0. 1,THF）（8b）; 2（5）-nitro and 3（4）-chloro isomers were separated. Meanwhile, the mechanisms for nucleophilic substitution （SN2Ar） reaction on the aromatic rings were explored. The ultraviolet spectra and fluorescence emission spectra of the synthesized compounds were determined; the relative fluorescence quantum yield （φf） was studied. The results show that the fluorescence efficiency, the Strokes shift and the molar absorption coefficient of the compounds are affected by conjugation and substituting groups.
出处
《应用化学》
CAS
CSCD
北大核心
2006年第3期283-288,共6页
Chinese Journal of Applied Chemistry
基金
广东省自然科学基金(011179)资助项目
关键词
苯并咪唑苯并异喹啉酮
萘酰亚胺
荧光量子产率
亲核取代反应
合成
benzimidazo [ 2,1-a ] benz [ de ] isoquinolinone, naphthalimide, fluorescence quantum yield, nucleophilic substitution reaction,synthesis
