Палладий-катализируемое аминирование мезо-бромофенилпорфиринов диаминами и аза-соединениями как метод синтеза строительных блоков для супрамолекулярных структур тема диссертации и автореферата по ВАК РФ 02.00.03, кандидат химических наук Михалицына, Елена Александровна

• Михалицына, Елена Александровна
• кандидат химических наук
• 2012

Оглавление диссертации кандидат химических наук Михалицына, Елена Александровна

Список сокращений.

1. Введение.

2. Литературный обзор.

2.1. Порфирины как строительные блоки в супрамолекулярных структурах.

2.2.Рс1-катализируемые реакции кросс-сочетания с образованием связи С -гетероатом (N, О, S, Se, Р, В).

2.3. Pd- катализируемая реакция аминирования (C-N кросс-сочетание по Бухвальду-Хартвигу).

2.4. Pd-катализируемые реакции амидирования.

2.5. Pd-катализируемые реакции С-0 кросс-сочетания (алкоксилирование и гидроксилирование).

2.6. Pd-катализируемые реакции С - S и С - Se кросс-сочетания (сульфанилирование и селенилирование).

2.7. Pd-катализируемые реакции С - Р кросс-сочетания (фосфорилирование).

2.8. Pd-катализируемая реакция кросс-сочетания с образованием связи С - В (реакция борилирования).

2.9. Синтез порфириновых димеров и олигомеров в ходе Pd - катализируемых реакций кросс-сочетания.

3. Обсуждение результатов.

3.1. Синтез и исследование структурных особенностей моно- и бис-бромофенилзамещённых порфиринов и их металлокомплексов.

3.2. Синтез и исследование мезо-моно- и бис(диамино)замещённых порфиринов.

3.2.1. Синтез и исследование свойств мезо- моно- и бис(этилендиаминфенил)и пиперазинфенил)замещённых порфиринов и их производных.

3.2.2. Синтез .мезо-5-(аза-15-краун-5-фенил) и 5,15-бис(аза-15-краун-5-фенил)замещённых порфиринов и изучение процесса димеризации в присутствии катионов К+ и экзобидентатного лиганда (DABCO).

3.2.3. Синтез мезо-моно- и бис(диаза-18-краун-6)замещённых порфиринов и изучение процесса димеризации в присутствии катионов Cs+ и алкилдиаммония.

3.2.4. Синтез мезо- моно- 1,4,7,10-тетраазациклододец-10-илфенилзамещённых порфиринов и их гетероядерных комплексов с катионами лантаноидов.

3.3. Синтез порфириновых димеров и тримеров в ходе последовательной и «one-pot» Pd-катализируемых реакций аминирования; изучение супрамолекулярной координации с катионами металлов, алкилдиаммония и экзобидентатным лигандом (DABCO).

3.4. Синтез порфириновых димеров и тримеров в ходе Pd-катализируемого аминирования бромофенилпорфиринов аминофенилпорфиринами.

3.5. Изучение фотоэлектрохимического поведения аминофенилпорфиринов.

4. Экспериментальная часть

4.1. Характеристика реактивов и материалов.

4.2. Методы исследования.

4.3. Синтез моно- и бис-бромофенилзамещённых порфиринов и их металлокомплексов.

4.4. Синтез мезо- моно и бис-1ч[,М-диметилэтилендиаминзамещённых порфиринов ZnP,l-DMEDA, ZnP,2-DMEDA, ZnP,2-(DMEDA)2, Sn(OH)2P,l-DMEDA.

4.5. Синтез мезо-моно-этилендиаминзамещённого порфирина ZnP,l-EDA.

4.6. Синтез мезо-моно- и бис-пиперазинфенилзамещённых порфиринов ZnP,l-PZ и ZnP,2-PZ и ZnP,2-(PZ)2.

4.7. Синтез мезо- 5-(аза-15-краун-5-фенил) и 5,15-бис(аза-15-краун-5-фенил) порфиринов.

4.8. Синтез мезо- моно- и бис-диаза-18-краун-б-фенилзамещённьгх порфиринов ZnP,l-DA18-C-6, ZnP,2-DA18-C-6 и ZnP,2-(DA18-C-6)2.

4.9. Синтез порфириновых димеров и тримеров. !.

4.10. А. Синтез мезо- моно-циклен-фенилзамещённых порфиринов ZnP,l

Cyclen и ZnP,2-Cyclen.

4.10. Б. Комплексы H2P,l-3DECM-Cyclen с ацетилацетанатами лантаноидов

Ьа(асас)з, Gd(acac)3, Еи(асас)з).

4.10.В. Металлокомплексы ZnP,l-3DECM-Cyclen-La(acac)3, ZnP,l-3DECM-Cyclen-Eu(acac)3 CuP,l-3DECM-Cyclen-Gd(acac)3,.

4.11. Синтез тетра-, ди- и моно-аминофенил порфиринов H2P(PhNH2)4, H2PMeS2(PhNH2)2, H2PMes3(PhNH2) и их цинковых комплексов.

4.12. Синтез тримера (ZnPMes2(PhNH)2-(ZiiP,l)2 и димера ZnPMes3PhNH-ZnP,l.

4.13. Спектрофотометрическое титрование.

4.14. ЯМР титрование.

4.15. Рентгеноструктурный анализ.

5. Выводы.

Введение диссертации (часть автореферата) на тему «Палладий-катализируемое аминирование мезо-бромофенилпорфиринов диаминами и аза-соединениями как метод синтеза строительных блоков для супрамолекулярных структур»

Создание новых материалов, имеющих сложную, управляемую на молекулярном уровне, супрамолекулярную структуру с заданными свойствами, для различных областей современной медицины, молекулярной оптики и электроники является одним из быстро и широко развивающихся направлений современной науки. В настоящее время активные исследования в области супрамолекулярной химии связаны с разработкой новых материалов на основе порфиринов, имеющих в своём составе координирующие фрагменты, например такие, как краун- и аза-краун-эфиры, которые способны к комплексообразованию с рядом катионов металлов за счёт множественных нековалентных взаимодействий. Варьируя набор периферийных заместителей и катионов металлов, можно управлять строением сложных архитектурных ансамблей и тем самым влиять на свойства материала в целом.

Одним из перспективных способов введения гетерозаместителей в мезо- и р-положения порфиринового макроцикла является палладий-катализируемое кросс-сочетание галогензамещённых порфиринов с N, О, Р, S нуклеофилами. Этот метод позволяет получить с высоким выходом производные порфиринов, трудно доступные другими путями.

К таким реакциям относится Pd-катализируемое аминирование галогенпорфиринов, которое позволяет получать амино- и азазамещённые порфирины. Кросс-сочетание порфиринов с диаминами может привести к образованию порфириновых димеров и тримеров, где в качестве линкеров, связывающих порфириновые фрагменты, выступает аминогруппа.

Сочетание в одной молекуле координирующих фрагментов различной природы (например, металлоцентра порфирина и амино- или аза-краун-эфирной группы заместителя) и возможность получения как мономерных, так и олигомерных конъюгатов с определённым числом порфириновых фрагментов, открывают широкие возможности для создания новых материалов с заданными свойствами.

В связи с этим, настоящая работа посвящена разработке простого и эффективного способа получения новых производных порфирина, в которых порфириновые макроциклы непосредственно связаны с фрагментами диаминов или аза-соединений, с использованием палладий-катализируемого аминирования моно- и бис(бромофенил)замещённых порфиринов, а также исследованию их супрамолекулярной координации с катионами различной природы и экзобидентатным азотсодержащим лигандом.

Заключение диссертации по теме «Органическая химия», Михалицына, Елена Александровна

5. Выводы

1. Впервые получены неизвестные ранее диамино-, аза-, диаза- и циклензамещённые порфириновые конъюгаты в ходе палладий-катализируемой реакции аминирования бромофенилпорфиринов с выходами до 95%.

2. Установлена зависимость образования моно- и диаминированных порфириновых производных от природы лиганда, соотношения катализатор/лиганд и времени реакции.

3. Разработаны методы направленного синтеза порфириновых димеров и тримеров, с использованием последовательной и «one-pot» Pd-катализируемой реакции аминирования бромофенилпорфиринов с выходами до 59 и 75% соответственно.

5. Проведены рентгеноструктурные исследования и установлены кристаллические структуры: 5-(4^1 A7Л0-тeтpaoкca-13-aзa-циклoпeнтaдeц-13-ил)-фeнил)-2,3,7,8,12,18-гeкcaмeтил-13,17-ди-н-пeнтил порфиринатов цинка(И) и меди(П) (ZnP,3 и СиР,3) и 5-(4-(N,N-flHMeTwi-N' -(2-аминоэтил)-аминофенил)-2,3,7,8,12,18-гексаметил-13,17-ди(н-пентил)порфирината цинка(П) (ZnP,l-DMEDA).

6. Получены супрамолекулярные сэндвичевые димеры аза- и диаза-краунзамещённых порфиринов с катионами калия, цезия, алкилдиаммония и экзобидентатным азотсодержащим лигандом DABCO, образование которых доказано с помощью спектрофотометрического и 'Н ЯМР титрования. Рассчитаны константы связывания комплексов (ZnP,3)2DABCO, (ZnP,5)2DABCO, (ZnP,3)2K+, [(ZnP,3)2DABCO]K+, (ZnP,5)2K22+, [(ZnP,5)2DABCO]K22+.

7. Получены супрамолекулярные хелатные комплексы порфириновых димеров (ZnP,l-EDA-Sn(OH)2P,l)Cu+ и (ZnP,l)2-EDA-DABCO и сэндвичевые димерные комплексы порфириновых димеров ZnP,l-DA18-C-6-NiP,l и ZnP,2-DA18-C-6-ZnP,l с катионами цезия(1), алкилдиаммония и экзобидентатным лигандом DABCO, образование которых доказано с помощью спектрофотометрического титрования.

8. Разработаны методы синтеза комплексов гетероядерного циклен-порфиринового лиганда MP,l-3DECM-Cyclert (M=Zn(II), Cu(II)) с катионами лантаноидов (Ln3+ = La3+, Eu3+, Gd3+) с выходом 56 - 88%.

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