NORBORNADIENE: SYNTHESIS AND APPLICATIONS

Bicyclo[2.2.1]hepta-2,5-diene or norbornadiene (NBD) is a bicyclic hydrocarbon molecule used in many fields of chemistry since its first synthesis in 1950. NBD is the precursor of Aldrin, an agrochemical that was commonly used as an insecticide until the end of the XX century. Norbornadiene is capable of interconverting into its isomer, quadricyclane (QC), by the incidence of ultraviolet light. After that, the QC can release heat to return to the initial stage of NBD. To increase the energy efficiency and to enable the reaction to occur at the solar light, chemists have synthesized a wide variety of NBD derivatives. Papers in more than seventy years have studied and reported the physical and chemical properties of those compounds and their applications as rocket fuel, solar energy cell, homogeneous catalysis, and agrochemicals published between 1950 and 2021. Even computational chemistry has been used to investigate the NBD derivatives synthetic routes, elucidation, and application. In addition, this review describes other applications of norbornadiene.

双环[2.2.1]庚-2,5-二烯（norbornadiene, NBD）是一种双环烃类分子，自1950年首次合成以来，已被应用于化学领域的诸多方向。NBD是艾氏剂（Aldrin）的前体，艾氏剂是一种曾在20世纪末广泛用作杀虫剂的农用化学品。降冰片二烯可在紫外线照射下发生异构化反应，转化为其异构体四环庚烷（quadricyclane, QC）；此后四环庚烷可通过释放热量，回到初始的降冰片二烯状态。为提升该反应的能量利用效率，并使其可在太阳光照射下发生，化学家们已合成了多种不同的NBD衍生物。1950年至2021年间发表的逾70年的研究文献，已对这类化合物的理化性质，以及其作为火箭燃料、太阳能电池材料、均相催化剂及农用化学品的应用进行了系统研究与报道。计算化学也被用于探究NBD衍生物的合成路线、结构解析及应用场景。此外，本综述还阐述了降冰片二烯的其他应用。